Category: alcohols-buliding-blocks

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. 4464-18-0, name is Benzene-1,3,5-triyltrimethanol. A new synthetic method of this compound is introduced below., name: Benzene-1,3,5-triyltrimethanol

1 ,3,5-Tris(hydroxymethyl)benzene 15 (927 mg, 5.12 mmol) was suspended in CH2CI2 (25 mL) and solid PCC (5.94g, 27.6 mmol) was added. After 30 minutes of stirring, the reaction was diluted with acetone (10 mL) and was allowed to stir for 3 hr at RT. TLC (10% MeOH, 90% CH2CI2 Rf=0.50) was used to determine if the reaction was complete. After the reaction was complete, the precipitated chromium salts were filtered off and washed with CH2CI2. The aqueous layer was extracted 3 times in CH2CI2 and saturated Na2CO3. The organic layers were combined and dried over anhydrous Na2SO4, filtered, and concentrated. Flash column chromatography (100% CH2CI2 Rf=0.4) gave 16 (272 mg, 1.68 mmol, 33%). 1H NMR (CDCI3): delta 10.21 (s, 3H), 8.63 (s, 3H).

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, 4464-18-0, Benzene-1,3,5-triyltrimethanol.

Reference:
Patent; UNIVERSITY OF CENTRAL FLORIDA RESEARCH FOUNDATION, INC.; PHANSTIEL, Otto; ARCHER, Jennifer, J.; WO2010/148390; (2010); A2;,
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Electric Literature of 24034-73-9 , The common heterocyclic compound, 24034-73-9, name is (2E,6E,10E)-3,7,11,15-Tetramethylhexadeca-2,6,10,14-tetraen-1-ol, molecular formula is C20H34O, 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.

[0294] The resulting 2E-conjugated ester 8 was reduced to the corresponding 2E-alcohol 9 by means of a lithium aluminum hydride (LAtI) treatment, which was then converted into the corresponding 2E,6ES 1 QE-geranylgeranyS bromide 10 by means of phosphorus tribromide (PBr3) treatment in ethyl ether (EE) or with Ph3P and CBr4 in acetonitriie (ACN) at 0C. Furthermore, the interaction of carbanion (derived from ethyl acetoacetate 5 and sodium ethoxide) with the bromide 10 at 0C afforded the desired 2E.6E, 10E-gerany{geranyl ketoester 11, a precursor needed for 5E.9E, 13E-geraByigeranyl acetone 1. The subsequent ester hydrolysis and decarboxylation of ketoester 11 using aq. 5N KOH at 80C yielded the requisite 5E.9E, 13E-geranyJgeranyl acetone 1. TLC Rf: 0.28 (5% Ethyl Acetate in Hexanes); LC Retention time: 16.68 min; MS (m e): 313 [M – 18 + H]+, 331 (MH]+, 353 [M – Kj,

The synthetic route of 24034-73-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; COYOTE PHARMACEUTICALS, INC.; SERIZAWA, Hiroaki; WO2014/107686; (2014); A1;,
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Electric Literature of 86770-74-3 , The common heterocyclic compound, 86770-74-3, name is 2-(2-(2-(2-Aminoethoxy)ethoxy)ethoxy)ethanol, molecular formula is C8H19NO4, 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.

To a solution of 1-7 and HATU (147 mg) in DMF (1 mL) was added dropwise DIEA (135 muL) and tetraethylene glycol monoamine (45 muL). After stirring at room temperature for 5 h, the reaction was quenched by 10% aqueous citric acid, and the reaction mixture was extracted with EtOAc. The organic phase was washed with 1N HCl, brine, and saturated NaHC03. After drying over MgSO4 and filtration, solvent was removed with a rotary evaporator, and the mixture was purified by silica gel chromatography (DCM: MeOH=30: 1) to afford 1-27 in 70% yield. Q-TOF LC/MS m/z 609.3797 [M+H]+ (calcd. 608.37 for C32H52N2O9 [M]+); 1HNMR (400 MHz, CDCl3) delta -0.45 (1H, m), 0.685 (1H, m), 0.825 (6H, m), 1.13 (9H, s), 1.27-1.64 (6H, m), 1.94 (1H, m), 2.05 (1H, m), 2.64 (2H, m), 3.38-3.91 (16H, m), 4.07 (1H, t, J=8 and 12 Hz ), 4.25 (1H, m), 4.99 (1H, m), 6.35-7.06 (4H, aromatic H); 13C NMR (100 MHz, CDC13) delta 21.45, 24.12, 25.92, 28.20, 30.00, 31.10, 38.40, 39.51, 40.65, 49.28, 50.18, 52.77, 61.65, 69.98, 70.22, 70.60, 70.90, 72.60, 73.92, 80.30, 120.40, 123.35, 129.95, 132.23, 132.46, 159.12, 171.62, 173.23, 174.34.

The synthetic route of 86770-74-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; YALE UNIVERSITY; THE UNITED STATES OF AMERICA as represented by THE DEPARTMENT OF VETERANS AFFAIRS; SADEGHI, Mehran; YE, Yunpeng; KIM, Hye-Yeong; HUANG, Henry (Yiyun); TOCZEK, Jakub; (85 pag.)WO2017/177144; (2017); A1;,
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Synthetic Route of 83647-43-2, 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.83647-43-2, name is (3-Bromo-2-methylphenyl)methanol, molecular formula is C8H9BrO, molecular weight is 201.0605, as common compound, the synthetic route is as follows.

To a flask charged with (3-bromo-2-methylphenyl)methanol (6.0 g, 30 mmol) was added a IM TFA solution of Thallium Trifiuoroacetate (16.2 g, 29.8 mmol). The mixture was stirred at RT overnight. Analysis by TLC showed no starting material remaining. The solvent was removed under vacuum, and the residue was pumped under high vacuum for 30 min to ensure complete removal of TFA. To the residue was then added Palladium(II) Chloride (529 mg, 2.98 mmol), Lithium Chloride (2.53 g, 59.7 mmol), Magnesium Oxide (2.41 g, 59.7 mmol), and MeOH (150 mL). The reaction was flushed with CO twice, and kept under CO at room temperature. Analysis by LC showed a big product spot within 2 hours. To this solution was added ethyl acetate to precipitate the salts. The black solution was filtered through a celite pad, washed with EtOAc, adsorbed onto silica and purified by silica gel chromatography to afford 5-bromo-4- methyl-2-benzofuran-l (3H)-one. 1H-NMR (500 MHz, CDCl3) delta ppm 7.71 (d, J= 8.0 Hz, IH), 7.58 (d, J= 8.0 Hz, IH), 5.25 (s, 2H), 2.37 (s, 3H).

The chemical industry reduces the impact on the environment during synthesis 83647-43-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK SHARP &; DOHME CORP.; PASTERNAK, Alexander; SHAHRIPOUR, Aurash; TANG, Haifeng; TEUMELSAN, Nardos, H.; YANG, Lihu; ZHU, Yuping; WALSH, Shawn, P.; WO2010/129379; (2010); A1;,
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Related Products of 101597-25-5, Adding some certain compound to certain chemical reactions, such as: 101597-25-5, name is 1,1-Bis(4-methoxyphenyl)prop-2-yn-1-ol,molecular formula is C17H16O3, 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 101597-25-5.

Analogously to a literature procedure32 TMSCl (0.30mL, 2.4mmol) was added to a solution of alkyne 11g27 (0.46g, 1.7mmol), DMAP (11mg, 0.090mmol) and TEA (0.38mL, 2.7mmol) in THF (3mL) at 25C. After stirring for 4h at 25C the mixture was quenched with 85 H2O, extracted with Et2O, dried with Na2SO4 and evaporated to dryness. The crude product was purified by flash chromatography with PE/EtOAc (97:3). Colorless oil (510mg, 88%). IR (Film): =3283, 3000, 2956, 2903, 2836, 1607, 1585, 1507, 1464, 1441, 1415, 1303, 1249, 1195, 1172, 1119, 1079, 1035, 1024, 1006, 936, 916, 883, 842, 806, 782, 756, 636cm-1. 1H NMR (500MHz, CD2Cl2) delta 0.11 (s, 9H), 2.93 (s, 1H), 3.77 (s, 6H), 6.79-6.84 (m, 4H), 7.41-7.46 (m, 4H) ppm. 13C NMR (126MHz, CD2Cl2) delta 1.75, 55.77, 75.35, 76.94, 87.31, 113.71, 127.71, 139.29, 159.44ppm. HRMS (EI): [M]+ calcd. for C20H24O3Si, 340.1495; found 340.1486.

According to the analysis of related databases, 101597-25-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Toth, Krisztian; Hoefner, Georg; Wanner, Klaus T.; Bioorganic and Medicinal Chemistry; vol. 26; 22; (2018); p. 5944 – 5961;,
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As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 647-42-7, name is 3,3,4,4,5,5,6,6,7,7,8,8,8-Tridecafluorooctan-1-ol, molecular formula is C8H5F13O, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. Application In Synthesis of 3,3,4,4,5,5,6,6,7,7,8,8,8-Tridecafluorooctan-1-ol

(3) In a 4-liter reactor equipped with electromagnetic stirring, a rectification column, a thermometer, a constant pressure dropping funnel, a separator, a condenser, etc., 2500 g of an intermediate product obtained by (2) (6.05 mol of a fluorine-containing alcohol) is added. 20 g of p-toluenesulfonic acid and 13 g of hydroquinone. StirThe temperature was raised to 90 C, and 413 g (5.74 mol) of acrylic acid was added dropwise thereto for 2 hours.At the end of the reaction, no significant water droplets were produced after 5 hours of continuous reaction.The fluorine-containing olefin and the unreacted fluoroalcohol are distilled off.Refining 2133 g of perfluorohexylethyl acrylate, the purity is 99.02%,The yield was 88.8%.

With the rapid development of chemical substances, we look forward to future research findings about 647-42-7.

Reference:
Patent; Jinan Qifu New Materials Co., Ltd.; Shandong Chemical Institute; Li Haijing; Zhang Liting; (6 pag.)CN108911983; (2018); A;,
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Application of 64372-62-9, 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. 64372-62-9, name is 2-Chloro-5-(trifluoromethyl)benzyl alcohol. A new synthetic method of this compound is introduced below.

A 3 M K2CO3 solution is prepared by adding solid K2CO3 (31 g, 0.22 mol) to water (100 mL). Cooling is applied to keep the solution at 20-25 C. (2-chloro-5-(trifluoromethyl)phenyl) methanol (compound of formula 13) (17.5 g, 84 mmol), and boronic acid 5 (Scheme 3 ) (18.1 g, 85 mmol) are added to the K2C03 followed by THF (100 mL) rinse. The solution is degassed by sparging with argon gas for 20 min. The catalyst, 1 ,1 bis(di-tert- butylphosphino)ferrocene palladium dichloride (300 mg, 0.55 mol%) is added. The organic layer tums dark brown immediately. The biphasic mixture is aged at 35-45 C with vigorous stirring for 32 hours. The mixture is cooled to room temperature and water (150 mL) is added, followed by petrol ether (150 mL) and the aqueous layer is removed. The organic layer was washed with water (2><200 mL) and filtered through silica gel and the solvent is removed under reduced pressure to yield brownish oil which is crystallized from heptane to give a pale white solid (28.5 g, 80%). mp 93.5-95.5 C; 1H NMR (CDCI3) delta 1.24 (d, J = 6.9 Hz, 6H), 1 .95 (t, J = 6.1 Hz, 1 H), 3.21 (sept, J = 6.9 Hz, 1 H), 3.73 (s, 3H), 4.49 (m, 2H), 6.68 (d, J = 12.0 Hz, 1 H), 6.99 (d, J = 8.6 Hz, 1 H), 7.30 (d, J = 7.9 Hz, 1 H), 7.59 (dd, J1 = 8.0 Hz, J2 = 1 .3 Hz, 1 H), 7.86 (d, J = 0.7 Hz, 1 H). The impurity (5'-ethyl-4'-fluoro-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl)methanol (~ 3 %), which is formed from 5-ethyl-4-fluoro-2-methoxyphenylboronic acid present in the starting material under the conditions described in Step 5, was detected in the product. These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,64372-62-9, its application will become more common. Reference:
Patent; LEK PHARMACEUTICALS D.D.; HUMLJAN, Jan; MARAS, Nenad; WO2013/91696; (2013); A1;,
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Adding a certain compound to certain chemical reactions, such as: 702-98-7, 2-Methyladamantan-2-ol, 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, Safety of 2-Methyladamantan-2-ol, blongs to alcohols-buliding-blocks compound. Safety of 2-Methyladamantan-2-ol

A reactor made of glass and equipped with a stirrer was charged with 9 L of toluene, 950 g of 2-methyladamantanol, 50 g of methacrylic acid and 5.3 g of cresol sulfonic acid. The resulting mixture was heated until the reflux of toluene occurred, followed by reflux for 2 hours while distilling off water, whereby 2-methyleneadamantane was prepared. After it was cooled to 50 C. and 8 L of toluene was distilled off from it under reduced pressure, the residue was cooled to 0 C. A methacrylate forming reaction was then caused by adding 1280 g of methacrylic acid and 83 g of boron trifluoride ethyl ether and stirring the resulting mixture for one hour. After the reaction mixture was washed with 6 L of a 10% aqueous sodium carbonate solution and 5 L of deionized water, toluene was distilled off at 70 C. under reduced pressure, whereby 1126 g of crude 2-methyladamantan-2-yl methacrylate was obtained. The resulting product contained 91.3 wt. % of 2-methyladamantan-2-yl methacrylate and 7.9 wt. % of 2-methyleneadamantane. The crude 2-methyladamantan-2-yl(meth)acrylate (100 g) thus obtained and 50 g of n-undecane (boiling point under atmospheric pressure: 194.5 C., coagulation point: -25.6 C., solubility of methyleneadamantane in 100 g of n-undecane at 0 C.: 101 g) were distilled at 60 C. and 1 mmHg by using a vacuum still and 61 g was distilled off in 60 minutes. The fraction thus distilled off contained 86% of 2-methyleneadamantane together with undecane. The distillation temperature was raised to 85 C. and 3.5 g was distilled off further in 10 minutes to adjust the amount of 2-methyleneadamantane remaining in the still to less than 1 wt. %. The residue in the still was then distilled at 125 C. and 1 mmHg, whereby 81.2 g of 2-methyladamantan-2-yl(meth)acrylate having a purity of 99.5 wt. % was obtained. The resulting product had a 2-methyleneadamantane content of 0.1 wt. %.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,702-98-7, 2-Methyladamantan-2-ol, and friends who are interested can also refer to it.

Reference:
Patent; Mitsubishi Chemical Corporation; US2008/51597; (2008); A1;,
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As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 39590-81-3, name is 1,1-Bis(Hydroxymethyl)cyclopropane, molecular formula is C5H10O2, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. SDS of cas: 39590-81-3

Thionyl chloride (3 mL, 42.2 mmol) was added dropwise to a solution of 6-bromo-2-(4-chloro-2- (methylsulfonyl)benzyl)-3-(4-chlorophenyl)-4-fluoro-3-hydroxyisoindolin-1 -one (Example 35, Step 4 ) (4.72 g, 8.44 mmol) in THF (50 mL) at 0 C under a nitrogen atmosphere. DMF (20 drops) were added and the orange solution was allowed to warm to rt over 1 d. The reaction mixture was concentrated in vacuo and dissolved in THF (40 mL). Cyclopropane-1 ,1 -diyldimethanol (1 .72 g, 16.9 mmol) was added followed by K2C03 (2.33 g, 16.9 mmol) and the orange mixture was stirred at rt under an atmosphere of nitrogen for 1 d. DCM and water were added and the layers separated. The aqueous layer was extracted with DCM and the combined organic layers were dried (phase separator) and concentrated in vacuo. The residue was purified by Biotage (30 – 35% EtOAc in iso-hexanes) to give the title compound (3.33 g, 61 %) as a pale yellow solid. NMR (400 MHz, DMSO) 8.01 (1 H, d), 7.95 (1 H, dd), 7.79 (1 H, d), 7.56 (1 H, dd), 7.36 (2H, d), 7.30 – 7.26 (3H, m), 5.01 – 4.90 (2H, m), 4.45 (1 H, t), 3.48 – 3.31 (2H, m), 3.29 (3H, s), 3.05 – 2.96 (2H, m), 0.42 – 0.40 (2H, m), 0.27 (1 H, d), 0.19 (1 H, dd).

With the rapid development of chemical substances, we look forward to future research findings about 39590-81-3.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; CANCER RESEARCH TECHNOLOGY LIMITED; CHESSARI, Gianni; HOWARD, Steven; BUCK, Ildiko Maria; CONS, Benjamin David; JOHNSON, Christopher Norbert; HOLVEY, Rhian Sara; REES, David Charles; ST. DENIS, Jeffrey David; TAMANINI, Emiliano; GOLDING, Bernard Thomas; HARDCASTLE, Ian Robert; CANO, Celine Florence; MILLER, Duncan Charles; CULLY, Sarah; NOBLE, Martin Edward Maentylae; OSBORNE, James Daniel; PEACH, Joanne; LEWIS, Arwel; HIRST, Kim Louise; WHITTAKER, Benjamin Paul; WATSON, David Wyn; MITCHELL, Dale Robert; (293 pag.)WO2017/55860; (2017); A1;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 2807-30-9, name is 2-Propoxyethanol, the common compound, a new synthetic route is introduced below. name: 2-Propoxyethanol

Compound 2 (100 mg,0.15 mmol) was treated with 30% HBr/acetic acid (5 ml), and theresulted solution was stirred at room temperature for 2 h. Severaltypes of alcohol (50 ml) were added to the solution, and themixture was stirred at 30e80 C for 4 h under N2 protection. Then50 mL of DCM was added and separated, the combined organiclayers were washed with water (3 50 mL). The solvent wasevaporated and the residue was dissolved in THF (5 mL). Theresulted solution was treated with 1M LiOH (0.75 mL, 0.75 mmol),and the resulting mixture was stirred at room temperature for1e2 h. 1 M HCl solution was added to the mixture until pH 3 wasattained. Then the suspensionwas extracted with DCM (3 50 mL).The combined organic layers were washed with water (3 50 mL)and dried over anhydrous Na2SO4. The organic solvent wasremoved under reduced pressure and the residue was purified bycolumn chromatography over silica gel to afford black solid 5e13.

The synthetic route of 2807-30-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chen, Dan-Ye; Chen, Zhi-Long; Gao, Ying-Hua; O’Shea, Donal F.; Wu, Dan; Wu, Xiao-Feng; Yan, Yi-Jia; Zhu, Wei; Zhu, Xue-Xue; European Journal of Medicinal Chemistry; vol. 187; (2020);,
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