Gorb, L. G.’s team published research in Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya in | CAS: 17236-59-8

Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya published new progress about 17236-59-8. 17236-59-8 belongs to alcohols-buliding-blocks, auxiliary class Thiophene,Alcohol, name is Thiophen-3-ol, and the molecular formula is C4H4OS, Application In Synthesis of 17236-59-8.

Gorb, L. G. published the artcileRelation between activity and selectivity in electrophilic substitution reactions of five-membered heteroaromatic compounds. 3. Electronic effects of substituents, Application In Synthesis of 17236-59-8, the publication is Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya (1983), 828-35, database is CAplus.

The activity and selectivity of the electrophilic reactions of monosubstituted benzenes, thiophenes, furans, and pyrrole were studied by calculating localization energies by the CNDO/2 MO method. Anal. of theor. and exptl. reactivity indexes indicated a difference in the transfer of substituent effects from the α and β positions of the 5-membered heterocycles. Orbital interactions must be calculated to explain the selectivity of electrophilic reactions of the 5-membered heterocycles.

Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya published new progress about 17236-59-8. 17236-59-8 belongs to alcohols-buliding-blocks, auxiliary class Thiophene,Alcohol, name is Thiophen-3-ol, and the molecular formula is C4H4OS, Application In Synthesis of 17236-59-8.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Shaaban, Heba’s team published research in Journal of Food Composition and Analysis in 110 | CAS: 80-09-1

Journal of Food Composition and Analysis published new progress about 80-09-1. 80-09-1 belongs to alcohols-buliding-blocks, auxiliary class Ploymers, name is 4,4′-Sulfonyldiphenol, and the molecular formula is C7H5Cl2NO, HPLC of Formula: 80-09-1.

Shaaban, Heba published the artcileSimultaneous determination of bisphenol A and its analogues in foodstuff using UPLC-MS/MS and assessment of their health risk in adult population, HPLC of Formula: 80-09-1, the publication is Journal of Food Composition and Analysis (2022), 104549, database is CAplus.

Replacing bisphenol A with its analogs may represent a risk to human health because of their potential synergic effects. In this study, a fast, sensitive and reliable UPLC-MS/MS method for the identification and quantification of bisphenol A, bisphenol F, bisphenol S, D8 and pergafast in foodstuff was developed and validated. Sample preparation and clean up were carried out using ultrasonic extraction followed by solid-phase extraction on Oasis HLB cartridges. The developed method was successfully applied for simultaneous determination of the target analytes in 140 food samples from various categories (including: vegetables, dairy products, seafood products, condiments, beverages, oils & fats and others). The recovery ranged from 80.3% to 103.8% with relative standard deviations not higher than 11.5%. Limits of detection were within the range of 0.003-0.015μg kg-1 under the optimized conditions. Bisphenol A was found in the majority of food samples (83%) with the highest concentration of 110μg kg-1. Canned food contained higher concentrations of total bisphenols (23.8μg kg-1) compared to food samples packed in plastic containers (7.68μg kg-1), paper (3.53μg kg-1) or glass (1.14μg kg-1). The estimated daily intake for the detected bisphenols was also calculated (286.7 and 307.8 ng kg-1 BW day-1) for male and female adults, resp. The dietary exposure to total bisphenols through foodstuffs investigated in this study were found to be higher than the recently updated tolerable daily intake value of BPA (0.04 ng kg-1 BW day-1). Also, the calculated hazard index was found to be higher than 1, indicating that the exposure to the detected bisphenols is more likely to cause risk to consumers through the dietary intake. To the best of our knowledge, this is the first report estimating the health risk associated with dietary exposure to bisphenol A and its analogs in Saudi Arabia.

Journal of Food Composition and Analysis published new progress about 80-09-1. 80-09-1 belongs to alcohols-buliding-blocks, auxiliary class Ploymers, name is 4,4′-Sulfonyldiphenol, and the molecular formula is C7H5Cl2NO, HPLC of Formula: 80-09-1.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Roth, A. R.’s team published research in Entomol. Research Branch, Agr. Research Service U.S. Dept. Agr. in ARS-33-2 | CAS: 70445-33-9

Entomol. Research Branch, Agr. Research Service U.S. Dept. Agr. published new progress about 70445-33-9. 70445-33-9 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic Chain, name is 3-((2-Ethylhexyl)oxy)propane-1,2-diol, and the molecular formula is C11H24O3, Computed Properties of 70445-33-9.

Roth, A. R. published the artcileTests of repellents against tabanids, Computed Properties of 70445-33-9, the publication is Entomol. Research Branch, Agr. Research Service U.S. Dept. Agr. (1954), 10 pp., database is CAplus.

With white mice as the host animals, 258 synthetic compounds were tested in the laboratory as repellents of the deer fly (Chrysops discalis). Only a few showed promise as long-lasting repellents, 2-amino-3-isobornyloxy-2-methyl-1-propanol and Santomerse DT being most effective. Five of the best materials, along with various pyrethrum and allethrin sprays, were tested against mixed populations of tabanids on calves in the field. The same 2 compounds were most effective. All materials tested except the pyrethrins damaged the hair and skin of the calves slightly. Pyrethrum sprays were very effective only at high concentrations

Entomol. Research Branch, Agr. Research Service U.S. Dept. Agr. published new progress about 70445-33-9. 70445-33-9 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic Chain, name is 3-((2-Ethylhexyl)oxy)propane-1,2-diol, and the molecular formula is C11H24O3, Computed Properties of 70445-33-9.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Campisi, Sebastiano’s team published research in ChemCatChem in 14 | CAS: 111-29-5

ChemCatChem published new progress about 111-29-5. 111-29-5 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic hydrocarbon chain,Alcohol,Ploymers, name is Pentane-1,5-diol, and the molecular formula is C5H12O2, Formula: C5H12O2.

Campisi, Sebastiano published the artcileFurfural Adsorption and Hydrogenation at the Oxide-Metal Interface: Evidence of the Support Influence on the Selectivity of Iridium-Based Catalysts, Formula: C5H12O2, the publication is ChemCatChem (2022), 14(6), e202101700, database is CAplus.

Here, tetrakis(hydroxymethyl)phosphonium chloride-protected colloidal iridium nanoparticles were deposited by sol-immobilization on three different supports (CeO2, NiO and TiO2) and were investigated for the liquid-phase direct hydrogenation (H2 atmosphere) and catalytic transfer hydrogenation – CTH (N2 atmosphere) of furfural to study the effect of the H donor. The occurrence of strong-metal support interactions in 1 wt % Ir/CeO2 catalyst, as disclosed by XPS, was revealed to be responsible for the high activity observed in the direct hydrogenation (81% conversion after 6 h) and for the unusual selectivity to 2-methylfuran (70%) under CTH conditions. On the other hand, Ir/NiO showed peculiar selectivity to tetrahydrofurfuryl alc. in both H2 and N2 atmospheres (71% and 70%, resp.). The d. functional theory calculations further showed that the unique selectivity of Ir/NiO may be ascribed to the adsorption properties of furfural on the support, which activates a dual-site hydrogenation mechanism.

ChemCatChem published new progress about 111-29-5. 111-29-5 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic hydrocarbon chain,Alcohol,Ploymers, name is Pentane-1,5-diol, and the molecular formula is C5H12O2, Formula: C5H12O2.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Divakar, K. J.’s team published research in Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) in | CAS: 596-38-3

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) published new progress about 596-38-3. 596-38-3 belongs to alcohols-buliding-blocks, auxiliary class Other Aromatic Heterocyclic,Benzene,Alcohol, name is 9-Phenyl-9H-xanthen-9-ol, and the molecular formula is C19H14O2, Name: 9-Phenyl-9H-xanthen-9-ol.

Divakar, K. J. published the artcileApproaches to the synthesis of 2′-thio analogs of pyrimidine ribosides, Name: 9-Phenyl-9H-xanthen-9-ol, the publication is Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) (1990), 969-74, database is CAplus.

Several methods to the title compounds, e.g., deoxymercaptouridine I (R = H) and deoxymercaptocytidine II, from sulfur-containing precursors, e.g., I (R = 4-MeOC6H4CH2), are reported.

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) published new progress about 596-38-3. 596-38-3 belongs to alcohols-buliding-blocks, auxiliary class Other Aromatic Heterocyclic,Benzene,Alcohol, name is 9-Phenyl-9H-xanthen-9-ol, and the molecular formula is C19H14O2, Name: 9-Phenyl-9H-xanthen-9-ol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Govindappagari, Shravya’s team published research in Obstetrics & Gynecology (Philadelphia, PA, United States) in 135 | CAS: 58551-69-2

Obstetrics & Gynecology (Philadelphia, PA, United States) published new progress about 58551-69-2. 58551-69-2 belongs to alcohols-buliding-blocks, auxiliary class Chiral,Alkenyl,Amine,Aliphatic cyclic hydrocarbon,Ester,Alcohol,Inhibitor,, name is 2-Amino-2-(hydroxymethyl)propane-1,3-diol (Z)-7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((S,E)-3-hydroxy-3-methyloct-1-en-1-yl)cyclopentyl)hept-5-enoic acid, and the molecular formula is C25H47NO8, Computed Properties of 58551-69-2.

Govindappagari, Shravya published the artcileMild Thrombocytopenia and Postpartum Hemorrhage in Nulliparous Women With Term, Singleton, Vertex Deliveries, Computed Properties of 58551-69-2, the publication is Obstetrics & Gynecology (Philadelphia, PA, United States) (2020), 135(6), 1338-1344, database is CAplus and MEDLINE.

Objective: To assess whether mild thrombocytopenia (platelet count 100-149 k/μL) is associated with an increased risk of postpartum hemorrhage. Methods: Nulliparous women with term, singleton, vertex pregnancies undergoing labor at our institution between August 2016 and Sept. 2017 were included. The primary exposure was mild thrombocytopenia, defined as platelet count 100-149 k/μL, and the comparator was normal platelet count (150 k/μL or greater). Those with severe thrombocytopenia (platelet count less than 100 k/μL) were excluded from anal. The primary outcome was postpartum hemorrhage, determined by International Classification of Diseases, Tenth Revision codes and the hospital discharge problem list. Secondary outcomes included use of uterotonic agents (methylergonovine maleate or carboprost tromethamine), total blood loss 1,000 mL or greater, and blood transfusion. Data were analyzed by t test, χ or Fisher exact test, and multivariable logistic regression, with significance at α <0.05. Results: We evaluated 2,845 eligible women, of whom 2,579 (90.2%) had normal platelet count 150 k/μL or greater, 266 (9.3%) had platelet count 100-149 k/μL (mild thrombocytopenia), and 13 (0.5%) had platelet count less than 100 k/μL (severe thrombocytopenia). Compared with women with normal platelet count, those with mild thrombocytopenia had a higher rate of postpartum hemorrhage (16.9% vs 8.5%, P<.001) and were more likely to have total blood loss 1,000 mL or greater (4.5% vs 1.7%, P=.002) and receive methylergonovine maleate (10.5% vs 5.9%, P=.003) or carboprost tromethamine (6.0% vs 1.6%, P<.001) or both (3.8% vs 1.0%, P<.001), but rates of blood transfusion were no different (1.9% vs 1.5%, P=.59). The association between mild thrombocytopenia and postpartum hemorrhage persisted after multivariable adjustment for potential confounders (adjusted odds ratio 2.2, 95% CI 1.5-3.2, P<.001). Conclusion: Among nulliparous women with term, singleton, vertex pregnancies undergoing labor, those with mild thrombocytopenia (platelet count 100-149 k/μL) had a twofold greater likelihood of postpartum hemorrhage compared with those with normal platelet count.

Obstetrics & Gynecology (Philadelphia, PA, United States) published new progress about 58551-69-2. 58551-69-2 belongs to alcohols-buliding-blocks, auxiliary class Chiral,Alkenyl,Amine,Aliphatic cyclic hydrocarbon,Ester,Alcohol,Inhibitor,, name is 2-Amino-2-(hydroxymethyl)propane-1,3-diol (Z)-7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((S,E)-3-hydroxy-3-methyloct-1-en-1-yl)cyclopentyl)hept-5-enoic acid, and the molecular formula is C25H47NO8, Computed Properties of 58551-69-2.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Suzuki, Yumena’s team published research in Biological & Pharmaceutical Bulletin in 42 | CAS: 86-48-6

Biological & Pharmaceutical Bulletin published new progress about 86-48-6. 86-48-6 belongs to alcohols-buliding-blocks, auxiliary class Organic Pigment,Natural product, name is 1-Hydroxy-2-naphthoic acid, and the molecular formula is C7H13BrSi, COA of Formula: C11H8O3.

Suzuki, Yumena published the artcileExploring novel cocrystalline forms of oxyresveratrol to enhance aqueous solubility and permeability across a cell monolayer, COA of Formula: C11H8O3, the publication is Biological & Pharmaceutical Bulletin (2019), 42(6), 1004-1012, database is CAplus and MEDLINE.

Oxyresveratrol (ORV) is a naturally extracted compound with many pharmacol. activities. However, information about the crystalline form is not known when considering the development of a form for oral dosage. Cocrystal engineering offers drug mol. understanding and drug solubility improvements. Thus, we attempted cocrystn. of ORV using 10 carboxylic acids as a coformer at a 1:1 M ratio. Each combination was processed with liquid-assisted grinding, solvent evaporation and a slurry method, then characterized by powder X-ray powder diffraction (PXRD), conventional and low-frequency Raman spectroscopy and thermal anal. The solubility, dissolution and permeation studies across Caco-2 cell monolayers were conducted to evaluate the ORV samples. A screening study revealed that an ORV and citric acid (CTA) cocrystal formed by Et acetate-assisted grinding had characteristic PXRD peaks (14.0 and 16.5°) compared to those of ORV dihydrate used as a starting material. Low-frequency Raman measurements, with peaks at 100 cm-1, distinguished potential cocrystals among three processing methods while conventional Raman could not. An endothermic melt (142.2°C) confirmed the formation of the novel crystalline complex. The solubility of the cocrystal in the dissolution media of pH 1.2 and 6.8 was approx. 1000μg/mL, a 1.3-fold increase compared to ORV alone. In vitro cytotoxicity studies showed that the cocrystal and phys. blend were not toxic at concentrations of 25 and 12.5μM ORV, resp. The ORV-CTA cocrystal enhanced the cellular transport of ORV across Caco-2 monolayers. Therefore, cocrystn. could be used to improve aqueous solubility and permeability, leading to better oral bioavailability of ORV.

Biological & Pharmaceutical Bulletin published new progress about 86-48-6. 86-48-6 belongs to alcohols-buliding-blocks, auxiliary class Organic Pigment,Natural product, name is 1-Hydroxy-2-naphthoic acid, and the molecular formula is C7H13BrSi, COA of Formula: C11H8O3.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Choudhury, Anup’s team published research in Polyhedron in 212 | CAS: 90-64-2

Polyhedron published new progress about 90-64-2. 90-64-2 belongs to alcohols-buliding-blocks, auxiliary class Carboxylic acid,Benzene,Alcohol,Natural product, name is 2-Hydroxy-2-phenylacetic acid, and the molecular formula is C8H8O3, SDS of cas: 90-64-2.

Choudhury, Anup published the artcileDinuclear dysprosium(III) complex derived from a multidentate bis-hydrazone Schiff base ligand: Synthesis, crystal structure and magnetic properties, SDS of cas: 90-64-2, the publication is Polyhedron (2022), 115603, database is CAplus.

Starting from phloroglucinol, a multidentate Schiff base ligand, H3L N, N’-((1E, 1’E)-(5-acetyl-2,4,6-trihydroxy-1,3-phenylene)bis(ethan-1-yl-1-ylidene)bis(2-hydroxy-2-phenylacetohydrazide)), decorated with multiple coordination sites was designed. A dinuclear dysprosium complex, [{Dy(L)(H2O)2}2]·4CH3OH·3H2O (1), was synthesized by employing this ligand and characterized by elemental anal., spectroscopic and structural investigations. Single crystal x-ray diffraction anal. reveals that 1 is a dinuclear Dy(III) complex with a large DyDy distance. Magnetic investigation shows the absence of slow relaxation of the magnetization in 1 owing to the lack of an axial crystal-field.

Polyhedron published new progress about 90-64-2. 90-64-2 belongs to alcohols-buliding-blocks, auxiliary class Carboxylic acid,Benzene,Alcohol,Natural product, name is 2-Hydroxy-2-phenylacetic acid, and the molecular formula is C8H8O3, SDS of cas: 90-64-2.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Tarif, Ejaj’s team published research in Journal of Chemical Physics in 151 | CAS: 85618-21-9

Journal of Chemical Physics published new progress about 85618-21-9. 85618-21-9 belongs to alcohols-buliding-blocks, auxiliary class Tetrahydropyran,Chiral,sulfides,Alcohol, name is (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(octylthio)tetrahydro-2H-pyran-3,4,5-triol, and the molecular formula is C6H8O3, Related Products of alcohols-buliding-blocks.

Tarif, Ejaj published the artcileDynamics at the non-ionic micelle/water interface: Impact of linkage substitution, Related Products of alcohols-buliding-blocks, the publication is Journal of Chemical Physics (2019), 151(15), 154902/1-154902/9, database is CAplus and MEDLINE.

The impact of atom substitution on the glycoside linkage bridging the head and the tail parts in a nonionic surfactant mol. on aqueous dynamics of the resultant micellar solutions has been explored, employing time-resolved fluorescence and dielec. relaxation (DR) measurements. We have utilized n-octyl-β-D-glucopyranoside (OG) and n-octyl-β-D-thioglucopyranoside (OTG) as nonionic surfactants where the oxygen atom in the glucopyranoside unit is substituted by a sulfur atom. The substitution impact is immediately reflected in the dynamic light scattering measurements of aqueous solutions where the estimated size of the OTG micelles is found to be approx. four times larger than the OG micelles. Steady state spectral features obtained by using a fluorescent probe solute, coumarin 153 (C153), in these micellar solutions are quite similar and indicate locations of the solute at the micelle/water interface for both the surfactants. Interestingly, significant differences in the rotational and solvation dynamics of C153 in these two micellar solutions have been registered. The corresponding DR measurements do not indicate any signature of relaxation typical of bound water. The absence of bound water is further supported by the differential scanning calorimetric measurements. However, the typical slow solvation time scale for aqueous micellar solutions has been observed for these surfactants. Fluctuations in the solute-interface interaction energy due to the solute motion has been argued to be the origin for this slow solvation component as DR measurements do not indicate the presence of qual. similar relaxation time scale in the medium. (c) 2019 American Institute of Physics.

Journal of Chemical Physics published new progress about 85618-21-9. 85618-21-9 belongs to alcohols-buliding-blocks, auxiliary class Tetrahydropyran,Chiral,sulfides,Alcohol, name is (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(octylthio)tetrahydro-2H-pyran-3,4,5-triol, and the molecular formula is C6H8O3, Related Products of alcohols-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Freudenberg, Karl’s team published research in Annalen der Chemie, Justus Liebigs in 584 | CAS: 70110-65-5

Annalen der Chemie, Justus Liebigs published new progress about 70110-65-5. 70110-65-5 belongs to alcohols-buliding-blocks, auxiliary class Benzene,Alcohol,Ether,Benzene Compounds, name is 2-Phenoxy-1-phenylpropane-1,3-diol, and the molecular formula is C15H16O3, Application In Synthesis of 70110-65-5.

Freudenberg, Karl published the artcileSynthetic experiments connected with lignin, Application In Synthesis of 70110-65-5, the publication is Annalen der Chemie, Justus Liebigs (1953), 40-53, database is CAplus.

The following model substances are in part related to the dimers obtained by F. in experiments with coniferyl alc. (C.A. 47, 12296g), which are considered “secondary building stones” in lignin formation. Veratraldehyde condensed with CH2(CO2H)2 gave quant. yields of 3,4-(MeO)2C6H3CH:CHCO2H, whose Et ester (obtained in 94% yield) with Br in CHCl3 in artificial light yielded the dibromide, m. 110°; this was refluxed 7-8 hrs. with 3 moles KOH in alc., cooled, filtered, neutralized gradually (at about 0°) with concentrated HCl, refiltered, and concentrated in vacuo. Any salts that had been filtered, combined with those separating on concentration, were dissolved in H2O and acidified with 20% H2SO4, giving 20-30% 3,4-(MeO)2C6H3CCCO 2H (I), m. 156° (Fulton and Robinson, J. Chem. Soc. 1903, 1463). Carefully purified 4,3-Me(MeO)C6H3OH (13.8 g.) and 50 cc. MeOH containing 2.3 g. Na, evaporated in vacuo, heated 5 hrs. at 100° with 22 g. I Me ester, 50 cc. PhMe, and 13.8 g. creosol, allowed to stand 12 hrs. at room temperature, extracted with Et2O, shaken repeatedly with aqueous H2SO4, and the excess creosol extracted from the Et2O with aqueous NaOH, followed by washing, drying, evaporation, and fractionation, gave 17 g. Me β-(3-methoxy-4-methylphenoxy)-3,4-dimethoxycinnamate (II), prisms, m. 107-8°. At -70 to -80°, 5 g. crude II in 100 cc. dry Et2O with 0.3 g. LiAlH4 in 26 cc. Et2O gave a precipitate which, when decomposed with H2SO4, yielded a mixture of creosol, dimethoxycinnamyl alc. (III), and α-(2-methoxy-4-methylphenoxy)-3,4-dimethoxycinnamyl alcohol (IV). III and IV could not be separated by distillation, or by adsorption in C6H6 on Al2O3 but the separation was effected on a paper chromatogram with C6H6 (Rf of III and IV being 0 and 0.9, resp.). IV was noncrystalline, but gave a red, crystalline p-PhN2C6H4CO derivative, m. 118-19°; and a crystalline phenyl-urethan, m. 134-5°. The phenylurethan of III m. 107-8°. PhOCH2CO2Me (22 g.) and 14 g. BzH reacted vigorously with 3 g. Na wire and 40 cc. dry Et2O. After 12 hrs. 8.2 g. glacial AcOH, 60 cc. H2O, and 20 cc. Et2O were added successively, giving 38% PhCH(OH)CH(OPh)CO2Na (V), the Et2O and alc. washings from which, when concentrated and esterified, yielded 48% PhCH:C(OPh)CO2Me (VI), b11 210°, m. 60-1°. The free acid from V, oil (not characterized) gave the Me ester (VII), m. 61° (from petr. ether); Ac derivative of VII, m. 69-70°; S-benzylthiuronium salt (corresponding to V), m. 188°. VI in Et2O, under N at -70° with LiAlH4, gradually warmed to -20° with aqueous H2SO4 gave PhCH:C(OPh)CH2OH, viscous oil; phenyl urethan, m. 104°. VII, similarly reduced (at -20°) gave PhCH(OH)CH(OPh)CH2OH, b1 197°, m. 74-5°. Using Giacosa’s technique [J. prakt. Chem. 19, 396(1879)] but with longer initial heating, creosol, ClCH2CO2H, and NaOH gave 67% 4,2-Me(MeO)C6H3OCH2CO2H, m. 115°; Me ester (VIII), b11 167°; amide, m. 134-5°. Veratraldehyde (15.8 g.), 20 g. VIII, and 2.2 g. powd. Na under Et2O, first cooled, then heated several hrs. on a steam bath and acidified with AcOH, gave 3,4-(MeO)2C6H3CH:CRCO2Me (IX) [R in this and other compounds = 4,2-Me(MeO)C6H3O], which, reduced with LiAlH4 at -70° yielded the alc., C19H22O5 (isolated by treating the intermediate salt, under Et2O, with Dry Ice), oil, setting to a resin; 3,5-dinitrobenzoale, yellow needles, m. 158-9° (from BuOH). When 15.8 g. veratraldehyde, 20 g. VIII, 2.2 g. Na, and 50 cc. Et2O were kept at about 0° and then acidified with aqueous AcOH, the product was a mixture, b0.01 225°, of IX and 3,4-(MeO)2C6H3(OH)CHRCO2Me, m. 137° (from aqueous MeOH). To 8 g. Na (powdered under 100 cc. absolute PhMe) were added successively 25 g. abs EtOH and 50 g. vanillin, and the resulting Na derivative was filtered, triturated with and suspended in PhMe, well-cooled, and treated with freshly distilled ClCH2OMe; this kept at least 6 hrs. at room temperature, washed with 2% NaOH, and fractionated gave 41 g. methoxymethylvanillin (X), b1.5 145-7°, m. 39-40°. Freshly prepared X (9.8 g.) fused with 10.5 g. VIII, the product cooled, treated with 1.15 g. Na wire and 40 cc. Et2O, allowed to stand overnight, 3.1 g. AcOH in 40 cc. H2O added, and the mixture extracted with Et2O gave 9 g. 4,3-(MeOCH2O)(MeO)C6H3CH(OH)CHRCO2Me, b0.05 175-7°. With 30 g. 14-day-old X (or with fresh X containing small amounts of vanillin), the reaction was sluggish and required heating for completion, giving as the principal product 3,4-MeO(MeOCH2O)C6H3CH: CRCO2Me (XI), m. 112-13° (from aqueous MeOH). With a drop of H2SO4, AcOH, and Ac2O, 2 g. XI at 0° gave, after 1.5 hrs., 1.3 g. 3,4-MeO(AcO)C6H3CH:CRCO2Me (XII), m. 80° (from aqueous EtOH); when cooling was omitted, but the reaction continued for 8 hrs., the yield of XII was 87%. XII reduced with LiAlH4 under N at -20°, followed by a fully described extensive purification, including chromatographic fractionation on powd. cellulose, gave 3,4-MeO(HO)C6H3CH:CRCH2OH (XIII), b0.0001 140° (bath temperature), prisms, m. 90-1° (from CH2Cl2-petr. ether). Hydrogenated in MeOH with 5% Pd-BaSO4, XII gave the dihydro derivative, C21H24C7, b0.01 197°, which, reduced with LiAlH4, yielded the dihydro derivative of XIII, C18H22O5, b0.01 150°. Vanillin (10 g.), 6.25 g. CH2ClCO2H, 8.5 g. KOH, and 30 cc. H2O heated 4 hrs. at 100° and acidified with aqueous HCl gave quantitatively 2,4-MeO(OHC)C6H3OCH2CO2H, m. 188-9° [Elkan, Ber. 19, 3045(1886)], 8 g. of which with 10 g. CH2(CO2H)2 in 50 cc. pyridine containing small amounts of piperidine heated 2 hrs. at 100° yielded quantitatively 3,4-MeO(HO2CCH2O)C6H3CH:CHCO2H, m. 234° (also formed in 73% yield from ferulic acid, CH2ClCO2H and NaOH); di-Me ester (XIV), m. 104-5°. Veratraldehyde, (3 g.), 5 g. XIV, 0.41 g. Na powder, 20 cc. Et2O, and several drops absolute MeOH, heated several hrs. and acidified with aqueous AcOH, gave 2 g. Me α-[2-methoxy-4-(β-carbomethoxyvinyl)phenoxy]-3,4-dimethoxycinnamate, b0.01 260°, m. 129°. XIV and X refluxed with Na in Et2O gave, after acidification and fractionation of the Et2O extract, 31% Me O-methoxymethyl-α-[2-methoxy-4-(β-carbomethoxyvinyl)phenoxy]ferulate (XV), b0.01 275°, m. 100-1° (from MeOH). By replacing the MeOCH2 group in XV by Ac, the O-Ac analog (XVI), C24H24O9, b0.0001 180° (bath temperature), m. 117-18°, was formed. XVI (18 g.) in Et2O reduced by stepwise addition of LiAlH4 at room temperature, followed by adding moist Et2O, Na2S2O4, and Dry Ice to the aqueous phase, and fractionation in high vacuum of the Et2O extract, gave about 100 mg. resinous. 3,4-MeO[3,4-MeO(HO)C6H3CH:C(CH2OH)O] C6H3CH:CHCH2OH (XVII). The tetrahydro derivative of XVI, sirup, b0.001 160° (bath temperature); the tetrahydro derivative of XVII, colorless sirup, b0.001 150° (bath temperature). Inasmuch as both acetone-lignin and the dehydrogenation polymers of coniferyl alc. yielded 1.5-2% HCHO when distilled with H2SO4, a similar treatment was applied to a number of the synthetic compounds listed above. None of these gave more than faint traces of HCHO, with the single exception of PhCH(OH)CH(OPh)CH2OH, which yielded 1.3% HCHO. From this and previous studies (C.A. 42, 882a). F. and M. have indicated what types of structure, in O-containing derivatives of PhPr, are capable of giving rise to HCHO. 19 references.

Annalen der Chemie, Justus Liebigs published new progress about 70110-65-5. 70110-65-5 belongs to alcohols-buliding-blocks, auxiliary class Benzene,Alcohol,Ether,Benzene Compounds, name is 2-Phenoxy-1-phenylpropane-1,3-diol, and the molecular formula is C15H16O3, Application In Synthesis of 70110-65-5.

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