Author: tianli

Fawcett, Alexander published the artcileStrain-Release-Driven Homologation of Boronic Esters: Application to the Modular Synthesis of Azetidines, Computed Properties of 608534-44-7, the publication is Journal of the American Chemical Society (2019), 141(11), 4573-4578, database is CAplus and MEDLINE.

Azetidines are important motifs in medicinal chem., but there are a limited number of methods for their synthesis. Herein, the authors present a new method for their modular construction by exploiting the high ring strain associated with azabicyclo[1.1.0]butane. Generation of azabicyclo[1.1.0]butyl lithium followed by its trapping with a boronic ester gives an intermediate boronate complex which, upon N-protonation with acetic acid, undergoes 1,2-migration with cleavage of the central C-N bond to relieve ring strain. The methodol. is applicable to primary, secondary, tertiary, aryl, and alkenyl boronic esters and occurs with complete stereospecificity. The homologated azetidinyl boronic esters can be further functionalized through reaction of the N-H azetidine, and through transformation of the boronic ester. The methodol. was applied to a short, stereoselective synthesis of the azetidine-containing pharmaceutical, cobimetinib.

Journal of the American Chemical Society published new progress about 608534-44-7. 608534-44-7 belongs to alcohols-buliding-blocks, auxiliary class Other Aromatic,Boronic acid and ester,Boronate Esters,Boronic Acids,Boronic acid and ester, name is 2-(2,3-Dihydro-1H-inden-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, and the molecular formula is C15H21BO2, Computed Properties of 608534-44-7.

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

Kavala, Veerababurao published the artcileSelf-Assembled Superstructure of Xanthene Derivatives, Quality Control of 596-38-3, the publication is Journal of Chemical Crystallography (2007), 37(8), 527-535, database is CAplus.

Various multi carbon homologations of 9-phenyl-9H-xanthen-9-ol were obtained through a C-C bond formation by reacting it with various enolizable ketones in the presence of 1,1′-(ethane-1,2-diyl)dipyridinium bistribromide (EDPBT). All the ten derivatives along with the starting xanthen-9-ol have been characterized by single crystal X-ray diffraction. They all form self-assembled superstructure in the solid state. The self-assembling patterns in these supramol. architectures were explained based on steric and electronic nature of the pendant arm.

Journal of Chemical Crystallography 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, Quality Control of 596-38-3.

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

Kavala, Veerababurao published the artcileSyntheses and regiochemistry of enol addition to 9-phenyl-9H-xanthen-9-ol, COA of Formula: C19H14O2, the publication is Tetrahedron (2008), 64(18), 3960-3965, database is CAplus.

Regioselective C-C bond formation of 9-phenyl-9H-xanthen-9-ol 1 with various enolizable ketones I-X in an acidic (HBr) medium, obtained by the reaction of 1,1′-(ethane-1,2-diyl)dipyridinium bistribromide (EDPBT) with ketone is observed Except for ketone, 4-methyl-pentan-2-one VII in all other cases examined the attack to xanthenyl carbocation is from the thermodynamically stable enolizable side of the unsym. ketones. In the case of 3-methyl-butan-2-one VIII the equilibrium is in favor of the more stable enolizable ketone, which has large steric factor, hence no reaction was observed during its addition to alc. 1.

Tetrahedron 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, COA of Formula: C19H14O2.

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

Lunsford, Carl D. published the artcilePreparation of 4-amino-1-butanols and some derivatives of pharmacological interest, Synthetic Route of 4543-95-7, the publication is Journal of Organic Chemistry (1957), 1225-8, database is CAplus.

The 4-alkylamino (I) and 4-dialkylamino-1-butanols (II) were prepared by LiAlH₄ reduction of the product from equimolar amounts of butyrolactone (III) and a primary or secondary amine. Use of 2 moles amine resulted in N,N’-symmetrically substituted putrescines. The 3-aminopropanols were prepared similarly by the substitution of propiolactone (IV) for III. The 3,4,5-trimethoxybenzoates, the diphenylacetates, and the benzhydryl ethers of some of the II and of N-3-hydroxypropylpiperidine (V) and their quaternary salts were prepared and their pharmacol. activity examined III (68.8 g.) and 104 g. NHBu₂ heated 4 hrs. at 150°, the mixture in Et₂O added dropwise to 25.1 g. LiAlH₄ in 300 ml. Et₂O, refluxed 1 hr., the excess hydride decomposed with H₂O, the mixture filtered, the filtrate concentrated, and the residue fractionated gave 97.4 g. II (di-Bu derivative), b₄₀ 172-5°. When the starting amine refluxed below 150°, the reaction with III was carried out at reflux until the pot temperature reached 150° where it was kept 4 hrs.; when the starting amine was NHMe₂ or NHEt₂ the reaction was run in a sealed tube at 150°. The following results were obtained in preparing I and II, RR’N(CH₂)₄OH (RR’N, b.p./mm., % yield, n²⁵_D, and d. given): BuNH, 80-0.5°/0.2, 44, 1.4503, 0.8900; PhCH₂NH, 137-40°/0.8, 56, 1.5288, -; Me₂N, 98°/22, 56, 1.4390, 0.8798; Et₂N, 83-5°/0.8, 80, 1.4460, 0.8653; Pr₂N, 114°/4.3, 77, 1.4472, 0.8723; Bu₂N, 135°/0.3, 62, 1.4502, 0.8616; (CH₂)₅N, 75°/0.2, 71, 1.4733, 0.9471. III (172 g.) and 180 g. NHMe₂ heated 4 hrs. at 200° in 2 sealed tubes, the mixture heated to 125° in vacuo, and reduced with 125 g. LiAlH₄ gave 86 g. N,N,N’,N’-tetramethylputrescine, b₂₈ 78-80°, n²⁵_D 1.4261, d₂₇ 0.7864; dipicrate, m. 203-5°. There was also a higher-boiling fraction which proved to be II (di-Me derivative). Similarly, 17.2 g. III, 34 g. piperidine, and 11.4 g. LiAlH₄ gave 25 g. 1,4-piperidinobutane, b_0.3 117-18°; HCl salt, m. above 300°. IV (28.4 g.) added dropwise to 34 g. piperidine at 5-10° and towards the end of the addition the temperature allowed to rise to 20°, the sirup dissolved in 100 ml. tetrahydrofuran and reduced as above with 11.4 g. LiAlH₄, and the product fractionally distilled gave 31 g. V, b₂₅ 117-22°, n²⁵_D 1.4750, d²⁹₂₅ 0.9585; 3,4,5-trimethoxybenzoate hydrochloride, 51% yield, m. 169-71°; diphenylacetate nitrate, 90% yield, m. 115-16°(H₂O); diphenylacetate-MeI, m. 144.5-46° (alc.); diphenylacetate-MeBr, m. 165-6° (iso-PrOH). The 3,4,5-trimethoxybenzoic acid and diphenylacetic acid esters of I and II were prepared from the acid chloride with I or II. 3,4,5-Trimethoxybenzoyl chloride (23 g.) in 50 ml. CHCl₃ refluxed 2 hrs. with 11.7 g. II (di-Me derivative), the residue partitioned between dilute HCl and Et₂O, the acid extract made alk. and extracted with Et₂O, dried, and separated gave 26 g. II 3,4,5-trimethoxybenzoate-HCl, m. 122-4°. The quaternary salts of both the esters and the ethers were prepared by addition of MeI or MeBr to the base in Et₂O. When crystallization did not occur spontaneously the Et₂O was decanted and the oil crystallized from a suitable solvent. The following RCO₂(CH₂)NR”R’₂X were thus formed (R, R’, R”, X, m.p., and % yield given): 3,4,5-(MeO)₃C₆H₂, Me, H, Cl, 122-4°, 75; 3,4,5-(MeO)₃C₆H₂, Et, H, Cl, 140-1°, 97; 3,4,5-(MeO)₃C₆H₂, Et, Me, I, 142.5-44°, 78; 3,4,5-(MeO)₃C₆H₂, Pr, H, Cl, 118-19°, 35; 3,4,5-(MeO)₃C₆H₂, Pr, Me, I, 115-17°, 37; 3,4,5-(MeO)₃C₆H₂, [R’₂ = (CH₂)₅], H, Cl, 156.5-57°, 83; 3,4,5-(MeO)₃C₆H₂, [R’₂ = = (CH₂)₅], Me, I, 171-3°, 35; Ph₂CH, [R’₂ = (CH₂)₅], H, Cl, 148-50°, 53; Ph₂CH, [R’₂ = (CH₂)₅], Me, I, 69-72°, 34; Ph₂CH, [R’₂ = (CH₂)₅], Me, Br, 144-6°, 61. Benzhydryl bromide (49.3 g.) and 69.2 g. 4-dipropylamino-1-butanol in 200 ml. PhMe refluxed 15 hrs., concentrated in vacuo, partitioned between 5% NaOH and Et₂O, the extract then extracted with 5% HCl, this made alk. with 20% NaOH, and extracted with Et₂O gave 39 g. unchanged II (alkyl = Pr) and 26 g. N-(4-benzhydryloxybutyl)-N,N-dipropylamine, b_1.5 175-7°. The following PhRCHO(CH₂)₄NR’R’ were similarly prepared (R, R’R’N, salt, b.p./mm., or m.p., and % yield given): Ph, Et₂N, -, 202-5°/1.4, 68; Ph, Et₂N, HBr, 109-11.5°, -; Ph, Et₂N, MeBr, 120-1°, 81; Ph, Bu₂N, -, 192-4°/1.5, 38; Ph, (CH₂)₅N, -, 217-20°/2.0, 46; Ph, (CH₂)₅N, HCl, 135.5-37°, -; Ph, (CH₂)₅N, MeI, 126-6.5°, 73; p-ClC₆H₄, Et₂N, citrate, 123-4°, 62.

Journal of Organic Chemistry published new progress about 4543-95-7. 4543-95-7 belongs to alcohols-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Alcohol, name is 4-(Butylamino)butan-1-ol, and the molecular formula is C8H19NO, Synthetic Route of 4543-95-7.

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

Smolobochkin, Andrey V. published the artcileSynthesis and evaluation of water-soluble 2-aryl-1-sulfonylpyrrolidine derivatives as bacterial biofilm formation inhibitors, SDS of cas: 6346-09-4, the publication is Chemistry & Biodiversity (2019), 16(1), n/a, database is CAplus and MEDLINE.

The approach to the novel 1-[(2-aminoethyl)sulfonyl]-2-arylpyrrolidines via unique intramol. cyclization/aza-Michael reactions of N-(4,4-diethoxybutyl)ethenesulfonamide have been developed, which benefits from high yields of target compounds, mild reaction conditions, usage of inexpensive and low-toxic reagents, and allows for wide variability in both amine and aryl moieties. Biotesting with whole-cell luminescent bacterial biosensors responding to DNA damage showed that all tested compounds are not genotoxic. Tested compounds differently affect the formation of biofilms by Vibrio aquamarinus DSM 26054. Some of the tested compounds were found to suppress the bacterial biofilms growth and thus are promising candidates for further studies.

Chemistry & Biodiversity published new progress about 6346-09-4. 6346-09-4 belongs to alcohols-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Ether, name is 4,4-Diethoxybutan-1-amine, and the molecular formula is C10H11NO4, SDS of cas: 6346-09-4.

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

Ueda, Yoshihiro published the artcileFunctional Group Tolerance in Organo-Catalytic Regioselective Acylation of Carbohydrates, SDS of cas: 85618-21-9, the publication is Journal of Organic Chemistry (2009), 74(22), 8802-8805, database is CAplus and MEDLINE.

Organo-catalytic regioselective acylation of mono- and disaccharides with various functionalized acid anhydrides has been developed. Acylation of octyl β-D-glucopyranoside with acid anhydrides derived from α-amino acids, cinnamic acid, and gallic acid took place at C(4)-OH with 67-94% regioselectivity in the presence of catalyst I. Regioselective acylation of disaccharides with functionalized acid anhydrides was also achieved with 78-94% selectivity. Especially, a disaccharide with seven free hydroxy groups (X = OH, R’ = H) underwent acylation at C(4)-OH with 78% regioselectivity in the presence of I. Thus, functional group tolerance in the regioselective acylation catalyzed by I was found to be high.

Journal of Organic Chemistry 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 C9H6BrNO, SDS of cas: 85618-21-9.

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

Kawabata, Takeo published the artcileA Catalytic One-Step Process for the Chemo- and Regioselective Acylation of Monosaccharides, SDS of cas: 85618-21-9, the publication is Journal of the American Chemical Society (2007), 129(42), 12890-12895, database is CAplus and MEDLINE.

An organo-catalytic method for the chemo- and regioselective acylation of monosaccharides has been developed. Treatment of octyl β-D-glucopyranoside with isobutyric anhydride in the presence of 10 mol % of a C₂-sym. chiral 4-pyrrolidinopyridine catalyst at -50 °C gave the 4-O-isobutyryl derivative as the sole product in 98% yield. Thus, chemoselective acylation, favoring a secondary hydroxyl group in the presence of a free primary hydroxyl group, and regioselective acylation, favoring one of three secondary hydroxyl groups, took place with perfect selectivity. A competitive acylation between octyl β-D-glucopyranoside and a primary alc. (2-phenylethanol) with 1.1 equiv of isobutyric anhydride in the presence of 4-pyrrolidinopyridine catalyst gave the 4-O-isobutyrate of octyl β-D-glucopyranoside with 99% regioselectivity in 98% yield, which indicates that acylation of the secondary hydroxyl group at C(4) of the carbohydrate proceeds in an accelerative manner. A possible mechanism, involving multiple hydrogen-bonding between 4-pyrrolidinopyridine catalyst and the monosaccharide, is proposed for the chemo- and regioselective acylation.

Journal of the American Chemical Society 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 C14H28O5S, SDS of cas: 85618-21-9.

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

Rahaman, Rubina published the artcileDioxygen reactivity of iron(II)-gentisate/1,4-dihydroxy-2-naphthoate complexes of N4 ligands: oxidative coupling of 1,4-dihydroxy-2-naphthoate, Synthetic Route of 86-48-6, the publication is Dalton Transactions (2019), 48(45), 16993-17004, database is CAplus and MEDLINE.

The influence of supporting ligands and co-ligands on the dioxygen reactivity of Fe(II) complexes, [(6-Me₃-TPA)Fe^II(GN-H)]⁺ (1), [(6-Me₃-TPA)Fe^II(DHN-H)]⁺ (1a), [(BPMEN)Fe^II(GN-H)]⁺ (2), [(BPMEN)Fe^II(DHN-H)]⁺ (2a), [(TBimA)Fe^II(GN-H)]⁺ (3), and [(TBimA)Fe^II(DHN-H)]⁺ (3a) (GN-H₂ = 2,5-dihydroxybenzoic acid and DHN-H₂ = 1,4-dihydroxy-2-naphthoic acid) of N4 ligands, is presented. The Fe(II)-gentisate complexes react with dioxygen to afford the corresponding Fe(III) species. On the contrary, DHN-H undergoes oxidative C-C coupling to form [2,2′-binaphthalene]-1,1′,4,4′-tetrone 3-hydroxy-3′-carboxylic acid (BNTHC) on 1a, and [2,2′-binaphthalene]-1,1′,4,4′-tetrone 3,3′-dicarboxylic acid (BNTD) on 2a and 3a. In each case, the reaction proceeds through an Fe(III)-DHN species. The x-ray single crystal structures of [(6-Me₃-TPA)Fe^II(BNTD)] (1^Ox) and [(BPMEN)Fe^II(BNTD)] (2^Ox) confirm the coupling of two DHN-H mols. The formation of Fe(III) product without any coupling of co-ligand from the complexes, [(BPMEN)Fe^II(HNA)]⁺ (2b) and [(BPMEN)Fe^II(5-OMeSA)]⁺ (2c) (HNA = 1-hydroxy-2-naphthoate, 5-OMeSA = 5-methoxysalicylate) confirms the importance of para-hydroxy group for the coupling reaction. The unusual coupling of DHN-H by the Fe(II) complexes of the neutral N4 ligands is distinctly different from the oxygenolytic aromatic C-C cleavage of DHN by the Fe(II) complex of a facial N3 ligand.

Dalton Transactions 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 C11H8O3, Synthetic Route of 86-48-6.

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

Weinstock, Leonard M. published the artcileSynthesis of the β-adrenergic blocking agent timolol from optically active precursors, SDS of cas: 30165-97-0, the publication is Journal of Organic Chemistry (1976), 41(19), 3121-4, database is CAplus and MEDLINE.

The β-adrenergic blocking agent, trimolol (I), was prepared from R-glyceraldehyde via catalytic hydrogenation over Pd in the presence of Me3CNH2. Treating with PHCHO and then with II in the presence of Me3COK and acid hydrolysis gave 50% I.

Journal of Organic Chemistry published new progress about 30165-97-0. 30165-97-0 belongs to alcohols-buliding-blocks, auxiliary class Morpholine,Thiadiazole,Alcohol, name is 4-Morpholino-1,2,5-thiadiazol-3-ol, and the molecular formula is C9H9NO, SDS of cas: 30165-97-0.

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

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 (R_f 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, b_0.01 225°, 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), b_1.5 145-7°, 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, b_0.05 175-7°. 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), b_0.0001 140° (bath temperature), prisms, m. 90-1° (from CH₂Cl₂-petr. ether). Hydrogenated in MeOH with 5% Pd-BaSO₄, XII gave the dihydro derivative, C₂₁H₂₄C₇, b_0.01 197°, which, reduced with LiAlH₄, yielded the dihydro derivative of XIII, C₁₈H₂₂O₅, b_0.01 150°. 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, b_0.01 260°, 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), b_0.01 275°, m. 100-1° (from MeOH). By replacing the MeOCH₂ group in XV by Ac, the O-Ac analog (XVI), C₂₄H₂₄O₉, b_0.0001 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, b_0.001 160° (bath temperature); the tetrahydro derivative of XVII, colorless sirup, b_0.001 150° (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.

Referemce:
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