Category: alcohols-buliding-blocks

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.162021-14-9, name is (2-Amino-9H-fluoren-9-yl)methanol, molecular formula is C14H13NO, molecular weight is 211.26, as common compound, the synthetic route is as follows.HPLC of Formula: C14H13NO

Example 4 Synthesis of tert-Butyldimethylsiloxy-9-methyl-2-aminofluorene 5.91 g Imidazole (86.8 mmol, 2.1 equiv) was dissolved in 24 ml dry DMF and stirred 10 min in an iced bath under argon atmosphere. 7.47 g tertButyldimethylsilyl chloride (49.6 mmol, 1.2 equiv) dissolved in dry DMF was added. After 15 min stirring on ice 8.73 g 9-Hydroxymethyl-2-amino fluorene (41.3 mmol) dissolved in 40 ml dry DMF was added drop wise under cooling and argon atmosphere. The reaction was continued 15 min on ice and then at room temperature. The reaction was monitored by TLC [title product Rf=0.6, PE-MTBE (1:2)]. After 2 hours the starting product [Rf=0.1 PE-MTBE (1:2)] had disappeared and the reaction mixture was diluted with 400 ml CH2Cl2 and 100 ml 5% NaHCO3 was added. The organic phase was washed with 5*200 ml H2O and dried over Na2SO4. CH2Cl2 was eliminated by rotary evaporation and DMF was eliminated by azeotropic distillation with toluene. The residual brown oil (13.4 g, 99% yield) was analyzed by NMR and was used without further purification. 1H NMR (200 MHz/DMSO) delta=7.67-7.40 (3H; m; 3*Ar-H); 7.34-7.00 (2H; m; 2*Ar-H); 6.81 (1H; s; 1*Ar-H); 6.59 (1*; dd; J=8.02 Hz & 1.83 Hz; 1*Ar-H); 5.19 (2H; s; NH2); 3.97-3.76 (2H; m; CH2); 3.75-3.57 (1H; m; CH); 0.88 (9H; s; 3*CH3); 0.03 (6H; s; 2*CH3) 13C NMR (50 MHz/DMSO) delta=148.40 (Ar-Cqu); 145.81 (Ar-Cqu); 143.67 (Ar-Cqu); 141.88 (Ar-Cqu); 129.08 (Ar-Cqu); 127.10 (Ar-CH); 124.97 (Ar-CH); 124.16 (Ar-CH); 120.47 (Ar-CH); 117.87 (Ar-CH); 113.22 (Ar-CH); 110.58 (Ar-CH); 66.04 (CH2-OH); 49.60 (C9); 25.88 (3*CH3; t-Bu); 18.04 (Cqu; t-Bu), -5.04 (2CH3; Si-CH3)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,162021-14-9, (2-Amino-9H-fluoren-9-yl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; Baxter International Inc.; Baxter Healthcare SA; US2009/5574; (2009); A1;,
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Synthetic Route of 6214-44-4, 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. 6214-44-4, name is (4-Ethoxyphenyl)methanol, molecular formula is C9H12O2, 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.

60% NaH (300 mg, 7.5 mmol) was added in one portion to a suspension of tert-butyl 8-[(4-methylpiperidin-1-yl)carbonyl]-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2- carboxylate (1.58 g, 3.98 mmol) in DMF (30 mL) at room temperature under nitrogen. The mixture was stirred at room temperature for 20 min, then a solution of 4-ethoxybenzyl chloride in DMF (10 mL) (freshly prepared from 4-ethoxybenzyl alcohol (1.10 g, 7.23 mmol) and SOCl2 (1.0 mL) in dichloromethane at 0C) was added at room temperature, and the reaction mixture was stirred at room temperature for 1 h. The solvent was removed in vacuo and the residue was dissolved in dichloromethane and washed with water, dried over sodium sulfate. Removal of solvent gave the crude product, which was purified on silica gel (0-50% EtOAc in dichloromethane) to give the desired product (1.40 mg, 66%). MS (M+l): 532.2.

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 6214-44-4, (4-Ethoxyphenyl)methanol.

Reference:
Patent; AstraZeneca AB; WO2006/101434; (2006); A1;,
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Application of 15852-73-0, 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 15852-73-0, name is (3-Bromophenyl)methanol. This compound has unique chemical properties. The synthetic route is as follows.

(d) 3-(3-HydroxymethyIphenyl)-5-/i’o-butyl-Lambdar-fer?’-butylthiophene-2-sulfonamide; A mixture of m-bromobenzyl alcohol (1.05 g, 5.80 mmol), 5-iso-butyl-2-(iV-tert- butylaminosulfonyl)thiophene-3-boronic acid (2.41 g, 7.55 mmol; see step (c))5 Pd(PPh3)4 (270 mg5 0.235 mmol), NaOH (19.1 mL, 1.5 M aq5 28.6 mmol), EtOH (5.0 mL) and toluene (30 mL) was stirred under N2 at 900C for about 4 h. After cooling, water (10 mL) was added to the reaction mixture and this was then extracted with ethyl acetate. The combined organic phase was dried and concentrated in vacuo. The crude product was purified on column EPO chromatography (EtOAc/hexane, 30:70) to give sub-title compound as a colourless syrup in 57percent yield (1.26 g, 3.31 mmol).1H NMR delta (CDCl3): 0.96 (d, J = 6.6 Hz, 6H), 0.98 (s, 9H), 1.82-2.00 (m, IH), 2.66 (d, J= 7.1 Hz, 2H)5 3.28 (br s, IH), 4.67 (s, 2H), 4.81 (br s, IH), 6.76 (s, IH), 7.30-7.50 (m, 3H)5 7.64 (s, IH).13C NMR delta (CDCl3): 22.1, 29.4, 30.4, 39.1, 54.4, 64.6, 127.1, 127.8, 128.5, 129.0, 134.9, 136.2, 141.2, 143.2, 148.2. MS (ESI) m/z: 382(M+1)+.IRv (neat, cm”1): 3498, 3286, 2958, 2870, 1465, 1313. Anal. Calcd. for C19H27NO3S2: C, 59.81; H, 7.13; N, 3.67. Found: C, 60.05; H, 7.31; N, 3.90.

According to the analysis of related databases, 15852-73-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VICORE PHARMA AB; WO2006/109048; (2006); A1;,
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Application of 4442-79-9, 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. 4442-79-9, name is 2-Cyclohexylethanol. A new synthetic method of this compound is introduced below.

General procedure: The PBr3 (1.5 equiv) was added to a solution of alkyl alcohol (1.0equiv) in anhydrous tetrahydrofuran (5.0 mL) at 0 C and then theice bath was removed and the reaction mixture was further stirredat room temperature for 5 h. Water (30.0 mL) was added and thenextracted with EtOAc, the combined organic extracts were driedwith Na2SO4, and the solvent was evaporated in vacuo to get titlecompound, suitable for the next step without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,4442-79-9, 2-Cyclohexylethanol, and friends who are interested can also refer to it.

Reference:
Article; Chen, Ying; Wu, Bolin; Hao, Yameng; Liu, Yunqi; Zhang, Zhili; Tian, Chao; Ning, Xianling; Guo, Ying; Liu, Junyi; Wang, Xiaowei; European Journal of Medicinal Chemistry; vol. 171; (2019); p. 420 – 433;,
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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.575-03-1, name is 7-Hydroxy-4-(trifluoromethyl)coumarin, molecular formula is C10H5F3O3, molecular weight is 230.1401, as common compound, the synthetic route is as follows.Recommanded Product: 7-Hydroxy-4-(trifluoromethyl)coumarin

The synthetic steps of 4-trifluoromethyl-7-propylenecarbonyloxycoumarin are as follows:(1) To 10 mL of a solution containing 0.5 mmol of 4-trifluoromethyl-7-hydroxycoumarin and 0.625 mmol of triethylamine in a tetrahydrofuran solution, slowly add 0.6 mmol of acryloyl chloride chloride to the reaction flask within 30 min. Dissolved in 5 mL of tetrahydrofuran), the temperature is controlled at 0 ° C;(2) After stirring for 1 hour under ice bath conditions, the temperature of the solution was raised to room temperature and stirred overnight. ;(3) The reaction solution was subjected to a solvent under reduced pressure, and the residue was purified by silica gel chromatography eluting with ethyl acetate-hexane (1:3 v/v)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,575-03-1, 7-Hydroxy-4-(trifluoromethyl)coumarin, and friends who are interested can also refer to it.

Reference:
Patent; Da Lianli Technology Changshu Institute Co., Ltd.; Cui Jingnan; Feng Lei; (12 pag.)CN103755672; (2016); B;,
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Reference of 100-86-7, 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 100-86-7 as follows.

General procedure: To cooled (0 C) 95% sulfuric acid (10 ml) and undermagnetic stirring, was added dropwise a benzonitrile (1.25eq). Then (500 mg, 3.33mmol) of tertiary alcohol1,1-dimethyl-2-phenylethanol (1, commercial product) in cyclohexane (10 ml) was added to the solution. Afterreturn to room temperature, the resulting mixture was stirred under reflux for 2.5 hours. Then, the solution iscooled at room temperature and versed on ice-cold water under magnetic stirring. The solution is alkalizedwith ammonia. The organic layer was extracted with dichloromethane (100 ml), washed with a saturatedaqueous NaCl solution, dried over sodium sulfate and filtered. The solvent was removed in vacuo and thecrude material was then purified by chromatography (silicia gel) to afford the imine as pure compound.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,100-86-7, its application will become more common.

Reference:
Article; Selmi, Awatef; Aydi, Rihab; Mosset, Paul; Gree, Rene; Kammoun, Majed; Arkivoc; vol. 2019; 5; (2019); p. 108 – 120;,
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Electric Literature of 144-19-4, 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.144-19-4, name is 2,2,4-Trimethyl-1,3-pentanediol, molecular formula is C8H18O2, molecular weight is 146.2273, as common compound, the synthetic route is as follows.

EXAMPLE 1 Preparation of 1-(2-methyl-2-propenyloxy)-2,2,4-trimethylpentan-3-ol: To a 1L flask equipped with a reflux condenser and a thermometer, was added 292.5 g (2.0 mol) of 2,2,4-trimethylpentan-1,3-diol, 352.0 g (4.4 mol) of 50% aqueous NaOH, and 6.45 g (20 mmol) of tetrabutyl ammonium bromide.This mixture was heated in an oil bath and when the reaction mixture reached 50 C., 199.2 g (2.2 mol) of methallyl chloride was added drop-wise over 50 minutes.During the addition, the oil bath temperature was gradually raised to 100 C. and the reaction was continued for an additional 3 hours at 100 C. The reaction mixture was cooled, quenched with 400 ml of water, and extracted twice with 100 ml of toluene.The combined organic layers were washed with 50 ml of saturated ammonium chloride and 50 ml of saturated sodium chloride and evaporated to give 408 g of crude 1-(2-methyl-2-propenyloxy)-2,2,4-trimethylpentan-3-ol.After reduced pressure distillation (71-80 C., 3 MmHg), 377.1 g (yield 94.1%) of 1-(2-methyl-2-propenyloxy)-2,2,4-trimethylpentan-3-ol was obtained. 1H-NMR (500 MHz, CDCl3, delta) ppm: 0.93 (d, J=6.8 Hz, 3H), 0.95 (s, 3H), 0.96 (s, 3H), 1.02 (d, J=6.9 Hz, 3H), 1.74 (s, 3H), 1.85-1.94 (m, 1H), 3.13 (d, J=3.8 Hz, 1H), 3.19 (d, J=8.7 Hz, 1H), 3.38-3.43 (m, 2H), 3.85 (s, 2H), 4.88 (s, 1H), 4.91 (s, 1H). IR (film) cm-1: 3501, 3077, 2961, 2873, 1657, 1472, 1455, 1414, 1369, 1259, 1171, 1093, 1032, 992, 899. [0042] MS (m/e): 200 (M+), 183, 167, 157, 145, 128, 110, 95, 85, 83, 73, 55, 43, 29.

Statistics shows that 144-19-4 is playing an increasingly important role. we look forward to future research findings about 2,2,4-Trimethyl-1,3-pentanediol.

Reference:
Patent; Takasago International Corporation; US2004/14633; (2004); 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. 431-38-9, name is 3-Amino-1,1,1-trifluoropropan-2-ol, molecular formula is C3H6F3NO, 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. Computed Properties of C3H6F3NO

EXAMPLE 20 17-(5-fluoropyridin-3-yl)-N-[(RS)-3,3,3-trifluoro-2-hydroxypropyl]oestra-1,3,5(10),16-tetraene-3-carboxamide Analogously to Example 8, 250 mg of 17-(5-fluoropyridin-3-yl)oestra-1,3,5(10),16-tetraene-3-carboxylic acid were reacted with 171 mg of 2-amino-1-(trifluoromethyl)ethan-1-ol to give 161 mg of the title compound. C27H28F4N2O2 UPLC analysis (Method 1) Rt=1.45 min, mass found ESI(+) 488.21. 1H NMR (300 MHz, DMSO-d6): delta [ppm]=0.99 (s, 3H), 1.35-1.80 (m, 5H), 1.85-1.97 (m, 1H), 2.05-2.21 (m, 2H), 2.25-2.43 (m, 3H), 2.81-2.95 (m, 2H), 3.18-3.26 (m, 1H), 3.49-3.62 (m, 1H), 4.07-4.22 (m, 1H), 6.40-6.30 (m, 1H), 6.45 (d, 1H), 7.33 (d, 1H), 7.52-7.62 (m, 2H), 7.64-7.73 (m, 1H), 8.43 (d, 1H), 8.47-8.51 (m, 1H), 8.55 (t, 1H).

With the rapid development of chemical substances, we look forward to future research findings about 431-38-9.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BOTHE, Ulrich; BUSEMANN, Matthias; BARAK, Naomi; ROTGERI, Andrea; FISCHER, Oliver Martin; MARQUARDT, Tobias; (41 pag.)US2016/24142; (2016); A1;,
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Application of 124-68-5, 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. 124-68-5, name is 2-Amino-2-methyl-1-propanol, molecular formula is C4H11NO, 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.

Intermediate 12: tert-butyl (l-hydroxy-2-meth lpropan-2-yl)carbamate – Preparation 2 To a solution of 2-amino-2-methylpropan-l-ol (500 g, 5.61 mol, Alfa) in THF (3.0 L) and water (1.0 L) was added Na2C03 (10.11 g, 95 mmol) and sodium bicarbonate (10.37 g, 123 mmol) and stirring continued at 0 QC. di-ferf-Butyl dicarbonate (1.56 L, 6.7 mol) was added. The reaction mixture was stirred at RT for 18 h. The THF layer was separated and the aqueous layer extracted with ethyl acetate (1.5 L). The combined organic layers were washed with brine solution (2 x 2 L), were dried over anhydrous Na2S04 and then concentrated under reduced pressure to afford crude title compound. The crude material was dissolved in petroleum ether (750 mL) and cooled to -50 C. The resulting solid was filtered and washed with petroleum ether to give the title compound (750 g) as a white solid. (0250) *H NMR (400 MHz, DMSO-d6) delta: 6.08 (1H, s), 4.67 (1H, t), 3.29 (2H, s), 1.37 (9H, s), 1.13 (6H, s).

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 124-68-5, 2-Amino-2-methyl-1-propanol.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; PATEL, Vipulkumar Kantibhai; LIVIA, Stefano; (126 pag.)WO2016/12916; (2016); A1;,
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Synthetic Route of 5343-92-0, 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. 5343-92-0, name is 1,2-Pentanediol, molecular formula is C5H12O2, 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.

In a 1000 mL reaction flask, add 67 g of 1,2-pentanediol, 600 mL of toluene, 149 g of triethylamine, 40 g of calcium oxide, and 4.3 g of tetra-n-butylammonium hydrogen sulfate. Maintain the internal temperature at 0 to 5C, and slowly add the mixture under stirring. Sulfuryl fluoride gas 72g was reacted for 2 hours, nitrogen gas was blown for 1 hour, filtered, and the filtrate was desolvated under reduced pressure to obtain a solid crude product. Toluene 200 mL, 15-crown-5 0.05 g, 18-crown-60.05 g was heated and refluxed to dissolve. Slowly to room temperature, filtration, drying product 77g, yield 71.9%.

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 5343-92-0, 1,2-Pentanediol.

Reference:
Patent; Shanghai Kangpeng Technology Co., Ltd.; Quzhou Kangpeng Chemical Co., Ltd.; Li Xiaoliang; He Li; Tian Zhong; Xiao Hang; (11 pag.)CN107629032; (2018); A;,
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