Month: March 2021

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.2009-83-8, name is 6-Chlorohexan-1-ol, molecular formula is C6H13ClO, molecular weight is 136.6198, as common compound, the synthetic route is as follows.SDS of cas: 2009-83-8

In a 100 mL three-necked flask, 2.73 g (0.01 mol) of Compound 1 was dissolved in 50 mL of dry DMF,2.09 g (0.015 mol) of 6-chlorohexanol was added,3 g (0.022 mol) of anhydrous potassium carbonate and a catalytic amount of a phase transfer catalyst 18-crown-6,The reaction was carried out under the protection of nitrogen at a temperature of 100 C. for 12 hours;The solid in the solution obtained after the reaction was removed by filtration and the DMF was distilled off under reduced pressure. The resulting residue was separated by column chromatography (silica gel of 200 to 300 mesh was used as a stationary phase,The mobile phase consisted of a mixture of petroleum ether and ethyl acetate with a volume ratio of petroleum ether to ethyl acetate of 5: 1 to give 2.76 g of compound 2 (pale yellow solid, 74% yield)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,2009-83-8, 6-Chlorohexan-1-ol, and friends who are interested can also refer to it.

Reference:
Patent; Chinese Academy Of Sciences Physics And Chemistry Technology Institute; Liu Xinhou; Si Peng; Zhen Zhen; Bo Shuhui; Deng Guowei; Huang Heyan; Peng Chengcheng; Xu Huajun; (23 pag.)CN104974151; (2017); B;,
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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. 217479-60-2, name is 2,4,6-Trichlorobenzyl alcohol. A new synthetic method of this compound is introduced below., name: 2,4,6-Trichlorobenzyl alcohol

PREPARATION EXAMPLE 4: N-rri -(2.4.6-trichlorophenvncvclopropyllmethvn-3- (trifluoromethyl)pyridine-2-carboxamide (Compound A29)Step 1 : 1 ,3,5-trichloro-2-(chloromethyl)benzeneTo a stirred solution of (2,4,6-trichlorophenyl)methanol (2g, 9.4574 mmol) in chloroform (20 mL) kept under N2 atmosphere, thionyl chloride (1 .25 ml_, 17.023 mmol), was added slowly at 0C over a period of 10 min followed by a catalytic amount of DMF (35 mg, 0.4733 mmol). The reaction mixture was allowed to stirred at RT for 2h.The reaction mixture was quenched with 10 mL of water; the aqueous layer is extracted with dichloromethane (3 times). The combined organic layer were washed with 5% Na2C03 solution (2*10 mL), followed by NaCI (10mL) and dried over Na2S04. The solvent was evaporated under reduced pressure to give an yellow oil (1.78 gr). The oil was diluted in EtOAc and washed twice with NaCI (3 mL), then dried over NaS04, filtrated and evaporated to give 1.58 g of desired product.1H-NMR (CDCI3): 7.4 (s, 2H); 4.8 (s, 2H).

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, 217479-60-2, 2,4,6-Trichlorobenzyl alcohol.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; LOISELEUR, Olivier; PITTERNA, Thomas; O’SULLIVAN, Anthony, Cornelius; LUKSCH, Torsten; KICKOVA, Anna; WO2013/64520; (2013); 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. 52059-53-7, name is 2-(3-Fluorophenyl)ethanol. A new synthetic method of this compound is introduced below., Application In Synthesis of 2-(3-Fluorophenyl)ethanol

A mixture of 2-(3-fluorophenyl)ethanol (0.052 mL, 0.419 mmol), NaH (0.017 g, 0.419 mmol), and (S)-isopropyl 2-(tert-butoxy)-2-(4-(4,4-dimethylpiperidin- 1 -yl)-5 ?,6?- difluoro-6-methyl-[3,3?-bipyridinj-5-yl)acetate (0.041 g, 0.084 mmol) in THF was stirred at ambient temperature for 1 h. Then, 5 M NaOH (0.167 mL, 0.837 mmol) was added andthe mixture was heated at 80 C for 2 h. After cooling to ambient temperature, the reaction was filtered. The cmde mixture was purified by preparative LC/MS to provide the product (23.4 mg, 49%). ?H NMR (500 MHz, DMSO-d6) 8.14 – 8.03 (m, 1H), 7.93 (d,J= 1.8Hz, 1H),7.70(dd,J 11.0, 1.8Hz, 1H),7.42-7.24(m, 1H),7.21 -6.97(m, 3H), 5.83 (s, 1H), 4.67 (t, J= 6.6 Hz, 2H), 3.18 -3.00 (m, 1H), 1.32 (br s, 3H), 1.14 (s, 1OH), 0.89 – 0.76 (m, 6H) [note: piper/dine protons not all visiblej. LCMS (M+1) =568.3.

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, 52059-53-7, 2-(3-Fluorophenyl)ethanol.

Reference:
Patent; VIIV HEALTHCARE UK (NO.5) LIMITED; BELEMA, Makonen; BOWSHER, Michael S.; DESKUS, Jeffrey A; EASTMAN, Kyle J.; GILLIS, Eric P; FRENNESSON, David B; IWUAGWU, Christiana; KADOW, John F.; NAIDU, B. Narasimhulu; PARCELLA, Kyle E.; PEESE, Kevin M; SAULNIER, Mark G; SIVAPRAKASAM, Prasanna; (463 pag.)WO2018/127800; (2018); A1;,
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Related Products of 100-86-7, 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.100-86-7, name is 2-Methyl-1-phenyl-2-propanol, molecular formula is C10H14O, molecular weight is 150.22, as common compound, the synthetic route is as follows.

50mL egg-shaped flask was added N – saccharin trifluoromethylthio group 1 (110mg, 0.39mmol), 2- methyl-3-phenyl propanol (45.0mg, 0.3mmol), 96muL triethylamine (0.69mmol), in dichloromethane (5 mL), at room temperature for 5min.After completion of the reaction, the reaction solution rapidly by about 6 millimeters silica gel column, the column with the amount of methylene chloride and washed twice, and the combined organic liquid, spin dry to give trifluoromethyl – (2-benzyl) isopropyl thio peroxide (62mg, 83% isolated yield).Purity by NMR identified more than 95%.Trifluoromethyl – (2-benzyl-yl) thio-isopropyl peroxy (((2-Methyl-1-phenylpropan-2-YL) Oxy) (trifluoromethyl) sulfane):

Statistics shows that 100-86-7 is playing an increasingly important role. we look forward to future research findings about 2-Methyl-1-phenyl-2-propanol.

Reference:
Patent; Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences; Chen, Qilong; Xu, Chunfa; (25 pag.)CN104945298; (2016); B;,
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Reference of 37585-25-4, 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 37585-25-4, name is (2-Amino-5-chlorophenyl)methanol. This compound has unique chemical properties. The synthetic route is as follows.

Oxidation of (2-amino-phenyl)-methanols (3) to 2-amino-benzaldehydes (4) -General procedure; [0082] (2-Amino-phenyl)-methanol (12 mmol) in dry diethyl ether (25 ml_) is added dropwise to a mixture of manganese dioxide (48 mmol) in dry diethyl ether (25 ml_) and the mixture is stirred at rt overnight. The solution is filtered through a celite and the solvent is removed at reduced pressure. The crude product is used in the next step without further purification.; 2-Amino-5-crtloro-benzaldehyde; Yield 99%; 1H NMR (CDCI3): 6.14 (br s, 2H); 6.61 (d, 9 Hz, 1 H); 7.25 (dd, 9 and 2 Hz, 1 H); 7.44 (d, 2 Hz, 1 H) and 9.80 (s, 1 H).

According to the analysis of related databases, 37585-25-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERZ PHARMA GMBH & CO KGAA; HENRICH, Markus; BAUER, Angela; NAGAL, Jens; SLADEK, Meik; PARSONS, Christopher, Graham, Raphael; DANYSZ, Wojciech; KRAUSS, Valerjans; ROZHKOVS, Jevgenijs; STARCHENKOVS, Igors; TRIFANOVA, Dina; WO2010/37533; (2010); A1;,
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Electric Literature of 873-76-7 , The common heterocyclic compound, 873-76-7, name is (4-Chlorophenyl)methanol, molecular formula is C7H7ClO, 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: p-Nitrobenzyl alcohol (0.25 g, 1.63 mmol) was dissolved in anhydrous CH2Cl2 under N2. Triethylamine (0.227 mL, 1.63 mmol) was added and the resulting solution was cooled to 0 C. S2Cl2 (65.3 muL, 0.82 mmol) was added dropwise over twenty minutes. The solution was stirred at 0 C for two hours before being allowed to equilibrate to room temperature for three hours. The reaction was quenched with dH2O, washed with 2 x 20 mL aliquots of brine. The aqueous phase was extracted with CH2Cl2 (2 x 10 mL), and the combined organic phase was dried over MgSO4, filtered, and concentrated under reduced pressure. Column chromatography with a 2.5:1 ratio of hexanes:ethyl acetate afforded the below compounds. [Note: Bis(p-nitrobenzyloxy) disulfide, bis(4-methoxybenzyloxy) disulfide, bis(4-tertbutylbenzyloxy) disulfide, and bis(4-benzyloxy) disulfide have been previously synthesized in another laboratory with reported spectra in Ref. [13]. With the exception of bis(4-benzyloxy) disulfide, all spectra reported was almost identical to those reported below. For bis(4-benzyloxy) disulfide, Ref. [13] incorrectly assigned the aromatic signals as d 7.39 (m, 15H) instead of our d 7.17 (m, 10H). In addition, bis(p-nitrobenzyloxy) disulfide, bis(4-methoxybenzyloxy) disulfide, bis(4-methylbenzyloxy) disulfide, bis(4-benzyloxy) disulfide, and bis(4-chlorobenzyloxy) disulfide were also reported in Ref. [4]. The mp. and NMR matched our samples. Bis(4-phenylbenzyloxy) disulfide was first synthesized and fully characterized in our laboratory in Ref. [16]. Bis(4-phenoxybenzyloxy) disulfide, bis(4-cyanobenzyloxy) disulfide, and bis(4-cyanobenzyloxy) disulfide all were previously synthesized and fully characterized from our laboratory and reportedin Ref. [18].

The synthetic route of 873-76-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Stoutenburg, Eric G.; Gryn’Ova, Ganna; Coote, Michelle L.; Priefer, Ronny; Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; vol. 136; PC; (2015); p. 1924 – 1931;,
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Reference of 61367-62-2, 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. 61367-62-2, name is 4-Bromo-3,5-dimethoxybenzyl alcohol. A new synthetic method of this compound is introduced below.

Production Example 12; 2-Bromo-1,3-dimethoxy-5-(methoxymethyl)benzene; Under cooling in an ice water bath, to a solution of (4-bromo-3,5-dimethoxyphenyl)methanol (118.8 g) in N,N-dimethylformamide (960 mL) was added sodium hydride (60percent oily; 24.7 g), and the mixture was stirred for 10 minutes. To this iodomethane (41.7 mL) was dropped. Thereafter, the reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into ice water (2.5 L), and extracted with ethyl acetate. The resulting organic layer was washed with saturated saline, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography, and from a fraction of n-hexane:ethyl acetate (4:1), 121.3 g of a title compound was obtained as colorless oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,61367-62-2, 4-Bromo-3,5-dimethoxybenzyl alcohol, and friends who are interested can also refer to it.

Reference:
Patent; Negi, Shigeto; Shimizu, Toshikazu; Kuroda, Hiroshi; Shimomura, Naoyuki; Sasho, Manabu; Hoshino, Yorihisa; Kubota, Manabu; US2007/191613; (2007); A1;,
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Electric Literature of 1805-32-9, 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. 1805-32-9, name is 3,4-Dichlorobenzyl alcohol, molecular formula is C7H6Cl2O, 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.

(2) To a solution of the compound (440 mg) obtained in Example 131-(1) in tetrahydrofuran (10 ml,), 3,4-dichlorobenzyl alcohol (354 mg) and N,N-diisopropyl ethyl amine (0.680 ml) were added, and the mixed solution was refluxed for eight hours. Furthermore, 3,4-dichlorobenzyl alcohol (354 mg) was added thereto, and the resulting solution was refluxed for eight hours. The solution was returned to room temperature, and ethyl acetate was added thereto. The resulting solution was washed with water, and then washed with a saturated saline solution. The organic layer was dried over anhydrous magnesium sulfate and evaporated under reduced pressure to remove the solvent. The resulting crude product was purified by column chromatography (neutral OH type silica gel, ethyl acetate In-hexane = 0 to 50%) to give methyl (1-{[4-({[(3,4-dichlorobenzyl)oxy]carbonyl}amino)phenyl]carbonyl}isoquinolin-4-yl) acetate (280 mg) as a pale yellow amorphous substance. 1H NMR (600 MHz, CHLOROFORM-d) d ppm 3.73 (s, 3H), 4.11 (s, 2 H), 5.15 (s, 2H), 6.99 (br. s., 1H), 7.20 – 8.25 (m, 11H), 8.51 (s, 1H)

According to the analysis of related databases, 1805-32-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Taisho Pharmaceutical Co., Ltd.; EP2377851; (2011); A1;,
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Adding a certain compound to certain chemical reactions, such as: 4704-94-3, 2-(Hydroxymethyl)propane-1,3-diol, 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, Formula: C4H10O3, blongs to alcohols-buliding-blocks compound. Formula: C4H10O3

A mixture of 2-(hydroxymethyl)-1,3-propanediol (4.09 g, 38.5 mmol), acetone (130 ml, 1.768 mmol) and 70percent perchloric acid (1.37 g, 9.55 mmol) was stirred for 21 hours at room temperature. The reaction mixture was concentrated after adjusting to pH 9 with concentrated ammonia. The residue was purified by silica gel column chromatography (silica gel: 100 g, elution solvent: heptane, heptane/ethyl acetate = 1/3) to obtain the target compound (4.83 g, yield: 85.8percent) as a colorless oily substance. 1H-NMR (400 MHz, DMSO-d6) deltappm: 1.29 (3H,s), 1.30 (3H,s), 1.64-1.74 (1H,m), 3.35-3.41 (2H,m), 3.61 (2H,dd,J=7,12 Hz), 3.82 (2H,dd,J=4,12 Hz), 4.54 (1H,t,J=5 Hz)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,4704-94-3, 2-(Hydroxymethyl)propane-1,3-diol, and friends who are interested can also refer to it.

Reference:
Patent; Eisai R&D Management Co., Ltd.; EP2065379; (2009); A1;,
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Reference of 27489-62-9, 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 27489-62-9, name is trans-4-Aminocyclohexanol. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of trans-4-aminohexanol (10 g, 87 mmol) and triethylamine (18 mL, 0.13 mol) in dichloromethane (44 mL), di (tert-butyl) dicarbonate (21 g, 96 mmol) was added under cooling on ice. After stirring the obtained solution at room temperature for 6.5 hours, water and 1 N hydrochloric acid were added to the reaction solution, and the obtained solution was extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and then concentrated under vacuum. The obtained crude product was purified by recrystallization with a mixed solvent of hexane/ethyl acetate, and the precipitated solid was recovered by filtration to obtain the title compound (13 g). 1H-NMR (400 MHz, CDCl3) delta (ppm): 1.12 – 1.21 (2H, m), 1.33 – 1.44 (11H, m), 1.97 – 2.01 (4H, m), 3.40 – 3.43 (1H, m), 3.60 – 3.61 (1H, m), 4.33 – 4.35 (1H, m).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 27489-62-9, trans-4-Aminocyclohexanol.

Reference:
Patent; Toray Industries, Inc.; NISHIO, Yukihiro; KUBOTA, Yuko; YAMAMOTO, Masashi; NISHIMURA, Yutaka; MASUDA, Tomohide; TSUTSUI, Hideyuki; OKIMURA, Keiichi; UDAGAWA, Syuji; KAINO, Mie; MEGURO, Hiroyuki; SEKIYA, Yumiko; (105 pag.)EP3345893; (2018); A1;,
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