Category: alcohols-buliding-blocks

Related Products of 112-27-6 , The common heterocyclic compound, 112-27-6, name is 2,2′-(Ethane-1,2-diylbis(oxy))diethanol, molecular formula is C6H14O4, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

Triethylenc glycol (17.5 mL, 19.7 g, 131.13 mmol. 5 eq) was dissolved in DCM (150 mL·} and trimethyiamine (5.48 mL, 3.98 g, 1.5 eq) and cooled to 0. TsCI (5.00 g, 26.23 mmol 1 eq) was then added and die reaction mixture stirred at room temperature tor 18 hours. The reaction was diluted into DCM and washed with water (3x) and brine (lx). The organic layer was dried over sodium sulfate and concentrated in. vacuo. The crude product was purified on silica (0-5% MeOH in DCM) to give compound 64 (6,89 g, 22,6 mmol) in 85% yield. lH NMR (400 MHz, Chloroform-t/) 6 7.80 (d, J – 8.3 Hz, 2H), 7.38 ~ 7.30 (m, 2H)S 4.23 4.14 (m, 2H), 3.71 (id, J = 5.3, 4.3 Hz, 4H), 3.66 – 3.55 (m, 6H), 2.45 (s, 3H). C NMR (101 MHz, cdcl3) 144.98, 133.09, 129,95, 128.09, 72.58, 70.91 , 70.44, 69.28, 68.84, 1.88, 2 /76.

The synthetic route of 112-27-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; YALE UNIVERSITY; SPIEGEL, David; CAIANIELLO, David; (247 pag.)WO2019/199621; (2019); A1;,
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Synthetic Route of 426831-32-5, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 426831-32-5, name is (5-Fluoro-2-methoxyphenyl)methanol. This compound has unique chemical properties. The synthetic route is as follows.

Step 2: To 43 (1 eq, 17.9 mmol, 2.8 g) in CHCU (18 ml_) at room temperature, added HBr (22 mL) and the reaction mixture was stirred 2h, then diluted with dichloromethan, washed with water then brine, dried over sodium sulfate, and concentrated in vacuo to give 44 (3.3 g) as an off-white solid.

According to the analysis of related databases, 426831-32-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SCHERING CORPORATION; BOGEN, Stephane, L.; MA, Yao; WANG, Yaolin; LAHUE, Brian Robert; NAIR, Latha, G.; SHIZUKA, Manami; VOSS, Matthew Ernst; KIROVA-SNOVER, Margarita; PAN, Weidong; TIAN, Yuan; KULKARNI, Bheemashankar, A.; GIBEAU, Craig, R.; LIU, Yuan; SCAPIN, Giovanna; RINDGEN, Diane; DOLL, Ronald, J.; GUZI, Timothy, J.; HICKLIN, Danny, J.; NOMEIR, Amin; SEIDEL-DUGAN, Cynthia; SHIPPS, Gerald, W., Jr.; MACCOSS, Malcolm; WO2011/46771; (2011); A1;,
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Adding a certain compound to certain chemical reactions, such as: 10160-24-4, 7-Bromo-1-heptanol, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, Application In Synthesis of 7-Bromo-1-heptanol, blongs to alcohols-buliding-blocks compound. Application In Synthesis of 7-Bromo-1-heptanol

To a stirred solution of (S)-3- (1-CARBAMOYL-1,1-DIPHENYLMETHYL)pyrrolidine (40 g, 142.7 mmol) and triethylamine (59.6 mL, 428 mmol) in acetonitrile (1. 1 L) at 40C under a nitrogen atmosphere was added 7-bromo-1-heptanol (24 mL, 146 mmol) in acetonitrile (100 mL) dropwise. The reaction mixture was heated to 50C for 9 hours. The reaction mixture was allowed to cool before removing the solvent under reduced pressure. The crude residue was dissolved in dichloromethane (500 mL) and the organic layer washed with saturated aqueous sodium bicarbonate (2 x 300 mL), followed by water (300 mL) and saturated aqueous sodium chloride (300 mL), and then dried over magnesium sulfate (10 g). The magnesium sulfate was filtered off and washed with dichloromethane (100 mL). The solvent was then removed in vacuo to give the crude product which was purified on a short column (SIO2) by varying the eluant from 19: 1: 0.1 to 3: 1: 0.1 CH2CL2/MEOH/NH40H to give 31.35 g of the title intermediate as a white solid (56% yield ; >95% purity by HPLC Method A).

The synthetic route of 10160-24-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THERAVANCE, INC.; WO2004/41806; (2004); A2;,
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Electric Literature of 756520-66-8, Adding some certain compound to certain chemical reactions, such as: 756520-66-8, name is 1-(2,6-Dichloro-3-fluorophenyl)ethanol,molecular formula is C8H7Cl2FO, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 756520-66-8.

To a stirred mixture of D8 (65.5mg, 0.43mmol) and A5 (81mg, 0.39mmol) in THF (5mL), was added Ph3P (152mg, 0.58mmol) under the protection of nitrogen. After being stirred at r.t. for Ih, the mixture was added DIAD (1 17mg, 0.58mmol) at 00C. The resulting mixture was stirred at r.t. for two days and evaporated. The residue was purified by column chromatography (PE:EA=20: l) to afford D9 (1 13mg, 86%).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 756520-66-8, 1-(2,6-Dichloro-3-fluorophenyl)ethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; XCOVERY, INC.; WO2008/88881; (2008); A1;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 23783-42-8, name is 2,5,8,11-Tetraoxatridecan-13-ol. A new synthetic method of this compound is introduced below., Safety of 2,5,8,11-Tetraoxatridecan-13-ol

Example 3. Allyl 2,2-bis(2,5,8,11,14-pentaoxadodecyl)-4,7,10,13,16-pentaoxatetradecyl ether (compound 5 of Scheme 1 wherein n=4) Tetraethyleneglycol monomethyl ether (1.91 ml, 9 mmol) dissolved in dry and degassed DMF (3.5 ml) was carefully added to sodium hydride (365 mg, 9 mmol) in dry and degassed DMF (15 ml) under nitrogen at 0 C using a syringe. The temperature was then raised to room temperature and the reaction mixture was stirred for another 30 min. Tribromide 4 (730 mg, 2.0 mmol, example 1) was then added and the temperature was raised to 100 C, After 14 h the reaction was completed and the temperature was decreased to room temperature whereupon the reaction mixture was slowly added to H2O (150 ml). The H2O-phase was washed with diethyl ether (2 x 50 ml). Sodium chloride was then added to the H2O-phase until saturation. The H2O-phase was extracted with EtOAc (4 x 50 ml) and the combined organic phases were washed with brine (2 x 30 ml). Sodium sulfate and charcoal was added to the organic phase. The clear organic phase was filtered and the volatile material was removed at reduced pressure. Column chromatography (EtOAc:MeOH 9:1) gave 1.05 g of the product. 1H-NMR (CDCl3); 5.90 (m, 1H), 5.20 (m, 2H), 3.94 (dt, 2H), 3.70-3.55 (m, 48H), 3.45 (s, 6H), 3.43 (s, 2H), 3.40 (s, 9H).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 23783-42-8, 2,5,8,11-Tetraoxatridecan-13-ol.

Reference:
Patent; Spago Imaging AB; Axelsson, Oskar; Ek, Fredrik; EP2573089; (2013); A1;,
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Related Products of 122763-67-1 ,Some common heterocyclic compound, 122763-67-1, molecular formula is C9H16O3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

Vinyl acetate (15.6mL, 169.6mmol) was added to a solution of 1 (9.75g, 56.7mmol) in pentane (120mL). Amano lipase (from Burkholderia cepacia (6.2g) and MS 4 (8.9g) were added and the suspension was stirred at 30C for 16h. The reaction mixture was monitored by TLC. The lipase and sieves were filtered and washed with Et2O. The solvent was removed and the crude product was purified by silica gel column chromatography (EtOAc/Petroleum ether 1:9) to afford 1 (R) (4.4g, 25.6mmol, 45%) and 3 (S) (5.1g, 23.8mmol, 42%). 1 (R): [alpha]20D=+4.1 (c=1.04, CHCl3). 1H NMR (250MHz, CDCl3): delta=5.83 (ddd, J=16.0, 10.5, 5.5Hz, 1H, CH=CHaHb), 5.25 (dt, J=17.2, 1.5Hz, 1H, CH=CHaHb), 5.09 (dt, J=10.5, 1.4Hz, 1H, CH=CHaHb), 4.45 (m, 1H, CHOH), 3.2 (br s, 1H, CHOH), 2.47 (dd, J=16.1, 4.7Hz, 1H, COCHaHb), 2.38 (dd, J=16.1, 7.7Hz, 1H, COCHaHb), 1.42 (s, 9H, t-Bu) ppm. 13C NMR (62.5MHz, CDCl3): delta=171.7, 139.0, 115.2, 81.4, 69.1, 42.2, 28.1ppm. IR (film): numax=3434, 2979, 2931, 1726, 1645, 1393, 1368, 1256, 1157, 1039, 993, 924, 842, 763cm-1. HRMS (ESI): calcd for C9H16O3 [M+Na]+ 195.0997 found 195.1002. 3 (S): [alpha]20D=-5.5 (c=1.09, CHCl3). 1H NMR (250MHz, CDCl3): delta=5.81 (ddd, J=17.0, 10.5, 6.2Hz, 1H, CH=CHaHb), 5.59 (m, 1H, CHOCOCH3), 5.28 (dt, J=17.2, 1.2Hz, 1H, CH=CHaHb), 5.18 (dt, J=10.5, 1.2Hz, 1H, CH=CHaHb), 2.60 (dd, J=15.3, 7.9Hz, 1H, tBuOCOCHaHb), 2.50 (dd, J=15.3, 5.9Hz, 1H, tBuOCOCHaHb), 2.04 (s, 3H, OCOCH3), 1.42 (s, 9H, t-Bu) ppm. 13C NMR (62.5MHz, CDCl3): delta=169.9, 169.1, 135.3, 117.4, 81.2, 71.2, 40.8, 28.1, 21.2ppm. IR (film): numax=2979, 2933, 1736, 1646, 1457, 1369, 1290, 1235, 1159, 1024, 991, 947, 847, 764cm-1. HRMS (ESI): calcd for C11H18O4 [M+Na]+ 237.1103 found 237.1109.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,122763-67-1, its application will become more common.

Reference:
Article; Menhour, Boudjema; Akong, Firmin Obounou; Mayon, Patrick; Ple, Karen; Bouquillon, Sandrine; Dorey, Stephan; Clement, Christophe; Deleu, Magali; Harakat, Dominique; Haudrechy, Arnaud; Tetrahedron; vol. 72; 47; (2016); p. 7488 – 7495;,
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Reference of 27129-87-9, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 27129-87-9 as follows.

1-(chloromethyl)-3,5-dimethylbenzene was prepared from (3,5-dimethylphenyl)methanol and thionyl chloride: thionyl chloride (300 muL, 4.13 mmol, 11.8 M) and (3,5-dimethylphenyl)methanol (50 muL, 0.39 mmol, 1.1 M) were added to a NMR tube, capped. Teflon wrapping around the cap of nmr tube was used to prevent reaction mixture from leaking out. The NMR tube was heated at reflux under air (100 C) for 10 min. After cooling to 23 C, the nmr cap was replaced by a septum and volatiles were removed under vacuum via a needle through the septum. A solution (300 muL) of (1,4-bis(trifluoromethyl)benzene in C6D6 was added to the product mixture for 1H{13C} NMR analysis. All (3,5-dimethylphenyl)methanol was converted at the end of reaction. 1H{13C} NMR chemical shifts of 1-(chloromethyl)-3,5-dimethylbenzene: 6.75 ppm (2H, arene CH, s), 6.68 ppm (1H, arene CH, s), 4.15 ppm (2H, CH2Cl, s), 2.04 ppm (6H, benzylic CH3, s). 13C{1H} NMR chemical shifts of 1-(chloromethyl)-3,5-dimethylbenzene: 138.3 (s), 138.8 ppm (s),130.7 ppm (s), 127.4 ppm (s), 46.97 ppm, 21.65 ppm (s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,27129-87-9, its application will become more common.

Reference:
Article; Zhou, Meng; Goldman, Alan S.; Molecules; vol. 20; 6; (2015); p. 10122 – 10130;,
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Related Products of 60666-70-8, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.60666-70-8, name is (2-Bromo-5-chlorophenyl)methanol, molecular formula is C7H6BrClO, molecular weight is 221.48, as common compound, the synthetic route is as follows.

A solution of the alcohol (1.0 mmol; 1.0 eq.) in dry THF (4 mL) in a round-bottomed flask, under inert atmosphere (N2), is treated with TEA (1.5 eq.) and a solution of methanesulfonic anhydride (1.5 eq.) in dry THF (1 mL) at 0C. The reaction mixture is stirred at rt and monitored by LC-MS. Upon reaction completion, the reaction mixture is concentrated under reduced pressure and diluted with EA and water. The layers are separated and the aq. layer is extracted with EA. The combined org. layers are washed with water and brine, dried over MgS04, filtered and concentrated under reduced pressure. Purification of the residue gives the desired product. Starting from intermediate S. l (23.48 g) and proceeding in analogy to Procedure AG, the title compound was obtained, without additional purification, as a white solid (34.53 g). 1H NMR (d6-DMSO) delta: 7.72 (d, J = 8.5 Hz, 1H); 7.67 (d, J = 2.6 Hz, 1H); 7.44 (dd, J = 8.5, 2.6 Hz, 1H); 5.27 (s, 2H); 3.29 (s, 3 H).

The chemical industry reduces the impact on the environment during synthesis 60666-70-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; BUR, Daniel; GUDE, Markus; HUBSCHWERLEN, Christian; PANCHAUD, Philippe; WO2011/121555; (2011); A1;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 68327-04-8, name is (1S,2S)-2-Aminocyclopentanol hydrochloride. A new synthetic method of this compound is introduced below., Quality Control of (1S,2S)-2-Aminocyclopentanol hydrochloride

To a chilled solution of 4-(5-(2,4-difluorobenzyl)-1-(2-fluorobenzyl)-2-oxo-1,2-dihydropyridin-3-yl)-4-hydroxy-2-oxobut-3-enoic acid (1) (150 mg, 0.338 mmol) in dimethylformamide (DMF) (2.0 mL), was added hydroxybenzotriazole (HOBT) (50 mg, 0.372 mmol), followed by 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI-HCl, 71 mg, 0.372 mmol) and the mixture was stirred for 30 min. A solution of (1S,2S)-(+)-trans-2-aminocyclopentanol hydrochloride and NaHCO3 (31 mg, 0.372 mmol) was added followed by stirring for 2 h at 0-5 C. Cold water was added to the reaction mixture, which was then extracted with ethyl acetate (2 × 20 mL). The combined organic phase was separated, washed with water twice, then once with 1 N HCl solution, and finally with saturated aqueous NaHCO3 solution. Concentration in vacuo afforded the crude product which was passed through a short silica gel column with chloroform as the eluting solvent. The eluent containing the product was concentrated and the resulting residue was triturated with hexanes, which afforded the product as a yellow solid in 117 mg (66%), mp 61-63 C, [alpha]20D[alpha]D20 +41.8 (c 0.01, methanol), UV lambdamax 396 nm (epsilon 14,455, methanol). 1H NMR (CDCl3, 500 MHz): delta 15.33 (br s, 1H), 8.16 (d, 1H, J = 2.0 Hz), 8.08 (s, 1H), 7.61-6.85 (m, 9H), 5.22 (s, 2H), 4.11 (m, 1H), 3.94 (m, 1H), 3.78 (s, 1H), 2.23 (m, 1H), 2.10 (m, 1H), 1.88 (m, 1H), 1.78 (m, 2H), 1.59 (m, 1H). 13C NMR (CDCl3, 125 MHz): delta 181.3, 180.6, 163.4, 163.3, 162.4, 162.1, 162.0, 161.4, 161.3, 160.4, 160.1, 160.0, 159.2, 145.5, 143.9, 142.3, 141.6, 132.4, 132.4, 132.3, 131.5, 131.4, 131.3, 131.3, 131.2, 130.7, 130.6, 125.0, 124.9, 124.8, 122.8, 122.7, 122.5, 122.2, 122.2, 122.1, 122.1, 117.1, 115.9, 115.7, 115.6, 111.9, 111.9, 111.8, 111.7, 104.7, 104.5, 104.3, 98.3, 79.5, 79.3, 61.0, 60.6, 51.5, 47.7, 47.3, 32.9, 32.8, 32.7, 30.8, 30.7, 30.5, 21.7, 21.5. HRMS: calcd for C28H26F3N2O5 (M+H), 527.1794; found 527.1799.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 68327-04-8, (1S,2S)-2-Aminocyclopentanol hydrochloride.

Reference:
Article; Okello, Maurice; Mishra, Sanjay; Nishonov, Malik; Nair, Vasu; Bioorganic and Medicinal Chemistry Letters; vol. 23; 14; (2013); p. 4112 – 4116;,
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Application of 1805-32-9 ,Some common heterocyclic compound, 1805-32-9, molecular formula is C7H6Cl2O, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

General procedure: To a solution of alcohol (1mmol) in 2mL of toluene was added GO (0.3g). The resulting mixture was sonicated in an Elmasonic P ultrasonic cleaning unit (ultrasonic bath) with a frequency of 37kHz and 100% output power at 80C for the time indicated in Table 4. Then Oxone (1mmol) and 2mL of an alcoholic solvent was added in the reaction medium and the resulting mixture was irradiated for the time indicated in Table 4. The mixture was filtered through a sintered funnel and evaporated under reduced pressure, and extracted with ethyl acetate. The organic layer was dried over Na2SO4, filtered and evaporated under reduced pressure. Purification was achieved by column chromatography using n-hexane/EtOAc: 100/3 as eluent. The spectroscopic data of the obtained esters were compared with authentic samples [5,40,42,43]. Spectroscopic data for methyl 3,4-dichlorobenzoate (entry 9, Table 4): Pale yellow, M.P. 44.7C; IR (KBr) nu=3089, 3022, 2958, 1729, 1589, 1435, 1378, 1301, 1110, 757cm-1; 1H NMR (300MHz, CDCl3) delta=3.94 (s, 3H, CH3), 7.53 (d, J=8.3Hz, 1H, CH Arom), 7.87 (dd, J=8.3, 1.9Hz, 1H, CH Arom), 8.13 (d, J=1.9Hz, 1H, CH Arom); 13C NMR (75MHz, CDCl3) delta=52.54, 128.63, 129.94, 130.52, 131.53, 132.92, 137.56, 165.21; MS (EI) (70eV), m/z (%): 208 (5) [M+4]+, 206 (31) [M+2]+, 204 (50) [M]+, 177 (10), 175 (62), 173 (100), 145 (30), 109 (20), 74 (18).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1805-32-9, its application will become more common.

Reference:
Article; Mirza-Aghayan, Maryam; Zonoubi, Somayeh; Molaee Tavana, Mahdieh; Boukherroub, Rabah; Ultrasonics Sonochemistry; vol. 22; (2015); p. 359 – 364;,
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