Category: alcohols-buliding-blocks

Synthetic Route of 40571-86-6, 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.40571-86-6, name is Trans-2-(benzylamino)cyclohexanol, molecular formula is C13H19NO, molecular weight is 205.2961, as common compound, the synthetic route is as follows.

B. (S)-Mandelic acid salt of (1R,2R)-2-trans-2-(benzylamino)cyclohexanol (3) and (R)-Mandelic acid salt of (1S,2S)-2-trans-2-(benzylamino)cyclohexanol (ent-3): A 1-L single-necked, roundbottomedflask containing equipped with a mechanical stirrer and apressure-equalising addition funnel was charged with the preparedethyl acetate solution (300 mL) containing amino alcohol rac-2, and asolution of (S)-mandelic acid (70.4 g, 0.46 mol, 0.5 equiv.) in EtOAc(150 mL) was added via the addition funnel over a period of 2 h atroom temperature. After the addition was complete the droppingfunnel was rinsed with EtOAc (2 ¡Á 5 mL) and the reaction mixture wasstirred overnight at ambient temperature, followed by 5 h at 0 C. Theprecipitated ammonium salt was collected by suction filtration, washedwith ethyl acetate (2 ¡Á 50 mL), and dried under reduced pressure at roomtemperature over 1 h to afford the (S)-mandelic acid salt of (1R,2R)-2-trans-2-(benzylamino)cyclohexanol (3) as a colourless solid (131.8 g,0.37 mol), yield 80% based on mandelic acid, m.p. 147-149 C (lit.10146 C); [alpha]D25 = +14.7 (c = 2.0, CHCl3); 1H NMR (CDCl3) delta 0.96-1.29(m, 4 H), 1.58-1.73 (m, 3 H), 1.90 (d, J = 12.6 Hz, 1 H), 2.53 (dt, J = 4.0,J = 12.0 Hz, 1 H), 3.03 (dt, J = 4.3, 10.6 Hz, 1 H), 3.46 (d, J = 12.9 Hz, 1H), 3.89 (d, J = 12.6 Hz, 1 H), 4.90 (s, 1 H), 7.19-7.35 (m, 8 H), 7.49-7.52(m, 2H). The filtrate from the above procedure was concentrated underreduced pressure to give a pale yellow oily residue (518.2 g) which wasdissolved in EtOAc (200 mL), transferred into a 1-L flask, and treatedwith a solution of (R)-mandelic acid ((70.4 g, 0.46 mol, 0.5 equiv.) inethyl acetate (100 mL) similar to the above described procedure, todeliver the (R)-mandelic acid salt of (1S,2S)-2-trans-2-(benzylamino)cyclohexanol (ent-3) as a colourless solid (132.8 g, 0.36 mol), yield 78%based on mandelic acid), [alpha]D25 = -15.3 (c = 2.0, CHCl3). The analyticaldata were in accordance with those observed for the correspondingenantiomer of opposite configuration.

The chemical industry reduces the impact on the environment during synthesis 40571-86-6, I believe this compound will play a more active role in future production and life.

Reference:
Article; Xue, Feng; Li, Chang-Gong; Zhu, Yong; Lou, Tian-Jun; Journal of Chemical Research; vol. 38; 5; (2014); p. 322 – 324;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Synthetic Route of 17100-58-2, Adding some certain compound to certain chemical reactions, such as: 17100-58-2, name is (4-Bromo-2-methylphenyl)methanol,molecular formula is C8H9BrO, 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 17100-58-2.

Scheme 1, step B: Methanesulfonyl chloride (171 mL, 2.11 mol) is added over 30 minutes to a mixture of (4-bromo-2-methyl-phenyl)methanol (250 g, 1.24 mol) and triethylamine (304 mL; 2.11 mol) in dichloromethane (2500 mL) cooled in ice/water. The mixture is allowed to warm to ambient temperature and is stirred for 16 hours. Water (5000 mL) is added and the product is extracted with dichloromethane (2*7000 mL). The combined organic layers are washed with saturated aqueous NaCl solution (5000 mL) and dried over Na2SO4 Filtration and concentration under reduced pressure provides a residue which is passed through a silica pad (eluting with hexane and ethyl acetate) to provide the title compound (234 g; 86% yield).

According to the analysis of related databases, 17100-58-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Eli Lilly and Company; QU, Fucheng; US2014/100179; (2014); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Application of 4740-78-7, 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. 4740-78-7, name is 1,3-Dioxan-5-ol, molecular formula is C4H8O3, 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.

Example 14 and Example 15; In 2 ml of tetrahydrofuran were dissolved 224 mg of the compound represented by the formula (IIa-1) and 125 mg of glycerol formal, 50 mg of sodium hydride was added under ice-cooling, and the mixture was stirred at room temperature for 2 hours. Thereafter, an aqueous saturated ammonium chloride was added to the reaction mixture, followed by extraction with t-butyl methyl ether. The organic layer was dried with sodium sulfate, and concentrated under reduced pressure. The residue was subjected to medium pressure preparative liquid chromatography to obtain 67 mg of a compound represented by the formula (14) :(hereinafter, referred to as present compound (14)) and 74 mg of a compound represented by the formula (15) :(hereinafter, referred to as present compound (15) . Present compound (14)1H-NMR (CDCl3, TMS) delta (ppm) : 5.07 (IH, s) , 4.93 (IH, s), 4.59 (2H, m) , 4.47 (IH, m) , 4.04 (IH, dd) , 3.79 (IH, dd) , ‘3.04 (6H, br)Present compound (15)1H-NMR (CDCl3, TMS) delta (ppm): 5.06 (IH, m) , 5.03 (IH, d) , 4.83 (IH, d) , 4.26 (2H, dd) , 4.08 (2H, dd) , 3.04 (6H, br)

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 4740-78-7, 1,3-Dioxan-5-ol.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; WO2008/32858; (2008); A2;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Synthetic Route of 4442-79-9 ,Some common heterocyclic compound, 4442-79-9, molecular formula is C8H16O, 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.

Example 10 l-(2-Cyclohexyl-l-hydroxyethyl)-2-phenyl-2,5-dihydro-4H-pyrazolo[3,4-c]quinolin-4-onePart A To a mixture of cyclohexylmethanol (5,0 mL, 36 mmol) and dichloromethane (27 mL) at 0 0C was added triethyl amine (27 mL), dimethyl sulfoxide (27 mL), and sulfur trioxide pyridine (8.5 g, 54 mmol). The reaction was stirred 2 hours before diluting with ethyl acetate and saturated aqueous ammonium chloride. The layers were separated and the aqueous layer was extracted with additional ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated to 12 g of cyclohexylacetaldehyde as a yellow oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4442-79-9, its application will become more common.

Reference:
Patent; 3M INNOVATIVE PROPERTIES COMPANY; WO2006/107771; (2006); A2;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

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 575-03-1, name is 7-Hydroxy-4-(trifluoromethyl)coumarin. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 7-Hydroxy-4-(trifluoromethyl)coumarin

2) 4.6 g of the product of step 1), 6 g of anhydrous potassium carbonate, 50 ml of acetone and 8.4 g of 1,3-dibromopropane were heated under reflux for 4 hours, and then cooled to room temperature and filtrated. The solvent was removed by rotation to give yellowish oil, which was passed through a column to give 5.6 g of white solid. Melting point: 72-74¡ãC, yield: 80.1 percent.

With the rapid development of chemical substances, we look forward to future research findings about 575-03-1.

Reference:
Patent; Huazhong University of Science and Technology; NHWA Pharma. Corporation; ZHANG, Guisen; CHEN, Yin; XU, Xiangqing; LIU, Bifeng; LIU, Xin; ZHAO, Song; LIU, Shicheng; YU, Minquan; ZHANG, Heng; LIU, Xinghua; EP2698369; (2014); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Reference of 13330-96-6, 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.13330-96-6, name is 4-(Dimethylamino)butan-1-ol, molecular formula is C6H15NO, molecular weight is 117.19, as common compound, the synthetic route is as follows.

General procedure: 12 (100 mg, 0.35 mmol) was dissolved in the mixture of 1,4-dioxane (10 mL) and H2O (2.00 mL) and then added with boronicacid (2.80 mmol), Pd(dppf)2Cl2 (28 mg, 0.035 mmol) and Cs2CO3(228 mg, 0.70 mmol). The reaction was heated at 100 C underargon atmosphere. After 12 h, the reaction mixture was cooled toroom temperature and was concentrated in vacuo. Then themixture was diluted with water and extracted with ethyl acetate.The combined organic layer was washed by saturated sodiumchloride solution for three times, dried over anhydrous Na2SO4 andconcentrated under reduced pressure. The residue was purified bysilica gel chromatography to give 13.To a stirred solution of 13 and triphosgene (100 mg, 0.34 mmol)in anhydrous dichloromethane (5 mL) was added triethylamine(104 mg, 1.02 mmol) at 0 C under nitrogen atmosphere. After5 min, a solution of 4-(dimethylamino)butan-1-ol (1.02 mmol) indichloromethane (5.00 mL) was added and then the mixture wasstirred at room temperature for overnight. The reactionwas dilutedwith dichloromethane (15 mL) and washed with water (3 20 mL).The organic phases were dried over anhydrous Na2SO4 andconcentrated in vacuo. The residue was purified by using columnchromatography to afford the corresponding product.

The chemical industry reduces the impact on the environment during synthesis 13330-96-6, I believe this compound will play a more active role in future production and life.

Reference:
Article; Lu, Dong; Liu, Jianan; Zhang, Yunzhe; Liu, Feifei; Zeng, Limin; Peng, Runze; Yang, Li; Ying, Huazhou; Tang, Wei; Chen, Wuhong; Zuo, Jianping; Tong, Xiankun; Liu, Tao; Hu, Youhong; European Journal of Medicinal Chemistry; vol. 145; (2018); p. 328 – 337;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 4728-12-5, name is (2,2-Dimethyl-1,3-dioxan-5-yl)methanol. This compound has unique chemical properties. The synthetic route is as follows. Formula: C7H14O3

To a solution of compound 24 (crude material max. 94 mmol)in dry DMF (600 ml) cooled to 0 C under argon atmosphere and NaH (60percent suspension in mineral oil; 6 g, 150 mmol, 1.6 eq.) was added. Reaction flask was filled with argon again and the mixture was stirred for 20 min. to preform sodium salt of alcohol. Benzylbromide (14.6 ml, 123 mmol, 1.3 eq.) was added and reaction flask was filled with argon again. The resulting mixture was let to warmto room temperature and stirred overnight. Water (100 ml) was added and mixture was stirred for 30 min. Solvent was evaporated in vacuo and the residue was codistilled with toluene (3). Crude material was suspended in EtOAc (250 ml) and mixture of saturatedsolution of NH4Cl (20 ml) and water (180 ml) was added.Water phase was extracted with EtOAc (2 150 ml). The organic phase was collected (250 + 150 + 150 ml) and washed with water(2 200 ml), followed by brine (1 200 ml) and dried overMgSO4. The solution was filtered and evaporated in vacuo. The residue(crude compound 25, red-brown oil) was diluted in MeOH(700 ml) and water (70 ml). DOWEX (50WX8 H+, 30 g) was addedand the mixture was heated at 50 C and stirred overnight. Reactionmixture was cooled down to room temperature and filteredthrough the frit (S3), evaporated in vacuo and codistilled withtoluene (3). Crude product 26 was obtained as brown oil andused in the next reaction step without purification. Reaction wasmonitored by TLC. Small amount of crude product was purifiedby flash chromatography (silica gel; eluent CHCl3/MeOH, gradient2?15percent) to obtain an analytical sample

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, 4728-12-5, (2,2-Dimethyl-1,3-dioxan-5-yl)methanol.

Reference:
Article; ?pa?ek, Petr; Keough, Dianne T.; Chavchich, Marina; Dra?insky, Martin; Janeba, Zlatko; Naesens, Lieve; Edstein, Michael D.; Guddat, Luke W.; Hockova, Dana; Bioorganic and Medicinal Chemistry; vol. 25; 15; (2017); p. 4008 – 4030;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Reference of 558-42-9, 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 558-42-9 as follows.

Example A65Preparation of intermediate 65: 1-(4-Iodo-pyrazol-1-yl)-2-methyl-propan-2-olA mixture of 4-iodopyrazole (3 g, 15.47 mmol), 1-chloro-2-methyl-2-propanol and cesium carbonate (8.06 g, 24.75 mmol) in N,N-dimethylformamide (30 ml) was stirred at 160¡ã C. for 40 min in a sealed tube, under microwave irradiation.The mixture was diluted with water and extracted with dichloromethane.The organic layer was separated, dried (Na2SO4), filtered and the solvents evaporated in vacuo.The crude product was purified by flash column chromatography (silica; ethyl acetate in heptane 20/80 to 40/60).The desired fractions were collected and concentrated in vacuo to yield intermediate 65 (3.98 g, 97percent) as a white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,558-42-9, its application will become more common.

Reference:
Patent; Pastor-Fernandez, Joaquin; Bartolome-Nebreda, Jose Manuel; Macdonald, Gregor James; Conde-Ceide, Susana; Delgado-Gonzalez, Oscar; Vanhoof, Greta Constantia Peter; Van Gool, Michiel Luc Maria; Martin-Martin, Maria Luz; Alonso-de Diego, Sergio-Alvar; Swinney, Kelly Ann; Leys, Carina; Weerts, Johan Erwin Edmond; Wuyts, Stijn; US2011/269752; (2011); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Reference of 23783-42-8 ,Some common heterocyclic compound, 23783-42-8, molecular formula is C9H20O5, 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.

A solution of para-toluenesulfonyl chloride (22.3 g, 105 mmol) in THF (35 mL) was added dropwise to a solution of tetraethylene glycol methyl ether (20.0 g, 96 mmol) and NaOH (6.7 g, 166 mmol) in a THF/H2O mixture (135 mL/45 ml) at 0 C. After stirring for one hour at 0 C., the reaction mixture was left to return to room temperature and then it was stirred for a further 20 hours. The solution was then poured into 200 ml of brine and the volatile materials were evaporated. The resultant mixture was extracted several times with dichloromethane and the combined organic phases were washed with brine, dried over MgSO4, filtered and evaporated under reduced pressure. The oily residue was purified by silica gel chromatography with a dichloromethane/methanol mixture (98/2) as eluent. Compound 32 is obtained in the form of a pale yellow oil in 96% yield (0310) 1H NMR (300 MHz, CDCl3) delta 2.39 (s, 3H, ArCH3), 3.31 (s, 3H, OCH3), 3.64 to 3.47 (m, 14H, OCH2CH2O), 4.11 to 4.08 (m, 2H, ArSO2OCH2), 7.28 (d, J=1.5 Hz, 2H, Ar-3,5-H), 7.73 (d, J=1.5 Hz, 2H, Ar-2,6-H); 13C NMR (75 MHz, CDCl3) delta 21.78, 59.14, 68.80, 69.45, 70.66, 70.73, 70.86, 72.07, 128.10, 129.99, 133.19, 144.96.

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. 23783-42-8, 2,5,8,11-Tetraoxatridecan-13-ol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UNIVERSITE DE STRASBOURG; UNIVERSITE CLAUDE BERNARD LYON 1; HOSPICES CIVILS DE LYON; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE -CNRS; FELDER-FLESCH, Delphine; BILLOTEY, Claire; PARAT, Audrey; GAROFALO, Antonio; KRYZA, David; JANIER, Marc; (138 pag.)US2016/221992; (2016); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Application of 100442-33-9, 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.100442-33-9, name is 1-(3,3-Diphenyl-N-methylpropylamino)-2-methyl-2-propanol, molecular formula is C20H27NO, molecular weight is 297.4345, as common compound, the synthetic route is as follows.

2,N-Dimethyl-N-(3,3-diphenylpropyl)-l-amino-2-propanol (5g) and methyl acetoactate (7.5g) were dissolved in xylene (50 ml) at 25-30C followed by the addition of zinc dust (1.75g). The reaction mixture was heated at 140-145C for 7 hours. Next,25 xylene was distilled out along with simultaneous addition of xylene in order to maintain the volume of xylene in the reaction mixture. The reaction mixture was cooled at 25- 30C followed by filtration to remove the catalyst. Distillation was carried out to remove xylene under reduced pressure. The resulting residue was degassed for 1 hour to produce title compound as viscous brown oil.

Statistics shows that 100442-33-9 is playing an increasingly important role. we look forward to future research findings about 1-(3,3-Diphenyl-N-methylpropylamino)-2-methyl-2-propanol.

Reference:
Patent; ACTAVIS GROUP PTC EHF; WO2008/107797; (2008); A2;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts