Tag: M.W=100-200

101-98-4, 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. 101-98-4, name is 2-(Benzyl(methyl)amino)ethanol. A new synthetic method of this compound is introduced below.

Preparation 5A; Alternately, the title compound was prepared by mesylation of N-benzyl-N-methyl ethanolamine, which was then reacted with biphenyl-2-ylcarbamic acid piperidin-4-yl ester in an alkylation reaction. A 500 mL flask (reactor flask) was charged with N-benzyl-N-methylethanolamine (24.5 mL), DCM (120 mL), NaOH (80 mL; 30 wt %) and tetrabutylammonium chloride. Mixing at low speed throughout the reaction, the mixture was cooled to -10 C. (cooling bath), and the addition funnel charged with DCM (30 mL) and mesyl chloride (15.85 mL), which was added drop wise at a constant rate over 30 minutes. The addition was exothermic, and stirring was continued for 15 minutes while the temperature equilibrated back to -10 C. The reaction was held for at least 10 minutes to ensure full hydrolysis of the excess mesyl chloride. A 250 mL flask was charged with biphenyl-2-ylcarbamic acid piperidin-4-yl ester (26 g; prepared as described in Preparation 3) and DCM (125 mL), stirred for 15 minutes at room temperature, and the mixture chilled briefly to 10 C. to form a slurry. The slurry was then charged into the reactor flask via the addition funnel. The cooling bath was removed and the reaction mixture was warmed to 5 C. The mixture was transferred to a separatory funnel, the layers allowed to settle, and the aqueous layer removed. The organic layer was transferred back to the reactor flask, stirring resumed, the mixture held to room temperature, and the reaction monitored by HPLC for a total of 3.5 hours. The reactor flask was charged with NaOH (1M solution; 100 mL), stirred, and the layers allowed to settle. The organic layer was separated, washed (NaCl satd. solution), its volume partially reduced under vacuum, and subjected to repeated IPA washings. The solids were collected and allowed to air-dry (25.85 g, 98% purity). Additional solids were obtained from further processing of the mother liquor (volume reduction, IPA, cooling).

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. 101-98-4, 2-(Benzyl(methyl)amino)ethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THERAVANCE, INC.; US2006/205777; (2006); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

100-86-7 , The common heterocyclic compound, 100-86-7, name is 2-Methyl-1-phenyl-2-propanol, molecular formula is C10H14O, 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 cooled (0 C) solution (7.5 mL) of sulfuric acid H2SO4 (95 %), 2mL of trichloroacetonitrile in 28 mL of hexane was added dropwise and under magnetic stirring. Then, (1.5 g, 9.98 mmol) of tertiary alcohol 1 (commercial product) in 15 mL of hexane was added to the solution. After a return to room temperature, the resulting mixture was stirred under reflux for 2.5 h. Then, the solution was cooled at room temperature and versed on ice-cold water (50 mL) under magnetic stirring. The solution is alkalized with ammonia. The organic layer was extracted with dichloromethane (100mL), washed with a saturated aqueous NaCl solution, dried over sodium sulfate, and filtered. The solvent was removed in vacuo and the crude material was then purified by chromatography (silica gel, eluent dichloromethane/methanol 95:5) to afford the imine 6 as pure compound. Yield: 90%. Mp: 74 C. 1H NMR (CDCl3, 300 MHz): delta(ppm) 1.27 (s, 6H, 2-CH3), 2.74 (s, 2H, CH2), 7.22 (d, J=8.7 Hz, 1H), 7.30(m, 1H), 7.38 (m, 1H), 8.11 (d, J=7.8 Hz, 1H). 13C NMR (CDCl3, 75 MHz): delta 26.75 (2C), 39.02, 55.74, 97.67, 122.79, 126.16, 127.60, 128.70, 131.20, 138.31, 157.90. IR (KBr): upsilon 2970 cm -1 (CH3), 1690 cm -1 (C=N), 1618 cm -1 (Ar). HRMS-ES [M+Na]+ calc. for C12H12NCl3 Na 297.9933; found 297.9929.

The synthetic route of 100-86-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Aydi, Rihab; Kammoun, Majed; Synthetic Communications; vol. 46; 2; (2016); p. 134 – 144;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

41175-50-2, 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. 41175-50-2, name is 1,2,3,5,6,7-Hexahydropyrido[3,2,1-ij]quinolin-8-ol, the common compound, a new synthetic route is introduced below.

(b) Take 2mL of anhydrous N,N-dimethylformamide, under ice bath and nitrogen protection, add phosphorus oxychloride (4mL) dropwise, stir for 30min, and add dropwise to the solution of intermediate 9 (1g Intermediate 9 was dissolved in 2 mL of anhydrous N,N-dimethylformamide), and after stirring for 10 min, the temperature was raised to 60C and the reaction was performed for 12 h. After cooling to room temperature, the reaction solution was poured into ice water, 1M NaOH was added to adjust the pH to 5-6. After standing for a period of time, a precipitate precipitated out, the reaction solution was suction filtered, and the crude product was obtained after drying, using column chromatography After purification, the eluent was methanol/dichloromethane (1:60) to obtain 0.9 g of a light green solid, that is, intermediate 10.

Statistics shows that 41175-50-2 is playing an increasingly important role. we look forward to future research findings about 1,2,3,5,6,7-Hexahydropyrido[3,2,1-ij]quinolin-8-ol.

Reference:
Patent; Sun Yat-sen University; Tan Jiaheng; Huang Zhishu; Yu Zeyi; Luo Wenhua; Chen Shuobin; (18 pag.)CN111116573; (2020); A;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

505-10-2, 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. 505-10-2, name is 3-(Methylthio)propan-1-ol. This compound has unique chemical properties. The synthetic route is as follows.

Step 1: synthesis of 3-(methylsulfonyl)propan-1-ol (intermediate 14a)3-(methylthio)propan-1-ol (200 g, 1900 mmol, CAS 5 05-10-2) was dissolved inCH2C12 (2000 mL). The mixture was cooled to 0C, then m-CPBA 85% in water (970g, 5700 mmol, CAS 937-14-4) was added portion wise keeping the temperaturebetween 0 and 5C. After addition, the mixture was allowed to warm to 25C and stirred for 15 h. The mixture was filtered through a celite pad and the filtrate was purified by flash column (Eluent: petroleum ether: ethyl acetate = 3:1 and then ethyl acetate: methanol = 10:1) to yield the intermediate 14a (75 g, 29%).

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 505-10-2, 3-(Methylthio)propan-1-ol.

Reference:
Patent; JANSSEN R&D IRELAND; TAHRI, Abdellah; VENDEVILLE, Sandrine Marie Helene; JONCKERS, Tim Hugo Maria; RABOISSON, Pierre Jean-Marie Bernard; HU, Lili; DEMIN, Samuel Dominique; COOYMANS, Ludwig Paul; WO2014/60411; (2014); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

100-37-8, 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. 100-37-8, name is 2-(Diethylamino)ethanol. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of N,N-diethylethanolamine (0.08 g, 0.7 mmol) (Aldrich) in DMF (5 mL) was added sodium hydride (0.028 g, 0.7 mmol). The mixture was stirred at room temperature for 30 minutes, and then 4-chloro-3-[(2-methanesulfonyl-7-oxo-7,8-dihydro-pyrido-pyrido[2,3-d]-pyrimidine-6-carbonyl)-amino]-benzoic acid methyl ester (0.044 g, 0.10 mmol) (from Example 32 supra) was added and the mixture was stirred at room temperature for 18 hours. The mixture was purified by HPLC eluting with MeCN/H2O to give 4-chloro-3-{[2-(2-diethylamino-ethoxy)-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidine-6-carbonyl]-amino}-benzoic acid. (Yield 0.030 g, 65.2%).

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 100-37-8, 2-(Diethylamino)ethanol.

Reference:
Patent; Anderson, Kevin; Chen, Yi; Chen, Zhi; Luk, Kin-Chun; Rossman, Pamela Loreen; Sun, Hongmao; Wovkulich, Peter Michael; US2012/184542; (2012); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 346-06-5, (2-(Trifluoromethyl)phenyl)methanol, 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, 346-06-5, blongs to alcohols-buliding-blocks compound. 346-06-5

Polystyrene triphenylphoshine (9.84 g, 1.58 mmol/gram, 15.5 mmol) was stirred in 100 mL of [DICHLOROMETHANE] for ten minutes. The regioisomeric mixture of methyl [5- (6-] { [(1,1-dimethylethyl)(diphenyl)silyl]oxy}-1H-benzimidazol-1-yl)-3-hydroxy-2- [THIOPHENECARBOXYLATE] and methyl [5- (5-] { [(1,1-dimethylethyl)-(diphenyl)silyl]oxy}-1H- [BENZIMIDAZOL-1-YL)-3-HYDROXY-2-THIOPHENECARBOXYLATE] (5.48 g, 10.4 mmol) was added in a single portion. 2-(Trifluromethyl)benzyl alcohol (1.68 mL, 12.6 mmol) was added via syringe, and the solution was cooled to [0] [OC.] [DI-TERT-BUTYL AZODICARBOXYLATE] (3.58 g, 15.5 mmol) was dissolved in 20 [ML OF DICHLOROMETHANE] and added dropwise via addition funnel. The reaction was warmed to room temperature and stirred for 1.5 hours. The mixture was filtered through filter paper, and the solid was washed with dichloromethane and methanol. The filtrate was concentrated and purified by flash chromatography to afford 2.89 g [(41percent)] of methyl 5-(5-{[(1, 1- dimethylethyl)(diphenyl)silyl]oxy}-1H-benzimidazol-1-yl)-3-({[2- [(TRIFLUOROMETHYL) PHENYL] METHYL} OXY)-2-THIOPHENECARBOXYLATE] and 2.69 g [(38percent)] of methyl [5- (6- { [ (1, 1-DIMETHYLETHYL) (DIPHENYL) SILYL] OXY}-1 H-BENZIMIDAZOL-1-YL)-3- ( { [2-] (trifluoromethyl)phenyl]methyl}oxy)-2-thiophenecarboxylate. Data for 5-OTBDPS regioisomer [:APOS;H] NMR (300 MHz, [DMSO-D6)] [8] 8.66 (s, 1 H), 7.98 (d, J = 7.6 Hz, 1 H), 7.86- 7.60 (m, 9H), 7.56-7. 44 (m, 6H), 7.01 (s, 1 H), 6.99 (dd, J = 6.7, 2.4 Hz, 1 H), 5.51 (s, 2H), 3.79 (s, 3H), 1.10 (s, 9H). MS [(ES+,] m/z) 687 [(M+1).] Data for 6-OTBDPS regioisomer: ‘H NMR (300 MHz, [DMSO-D6)] 8 8.60 (s, [1 H),] 7.99 (d, J= 7.6 Hz, [1 H),] 7.87-7. 57 (m, 9H), 7.54-7. 42 (m, 6H), 7.07 (d, J = 2.0 Hz, 1 H), 6.92 [(DD,] J = 8.8, 2.3 Hz, 1 H), 5.46 (s, 2H), 3.84 (s, [3H),] 1.11 (s, 9H). MS [(ES+,] m/z) 687 [(M+1).]

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,346-06-5, its application will become more common.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2004/14899; (2004); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

3597-91-9, 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. 3597-91-9, name is [1,1′-Biphenyl]-4-ylmethanol, molecular formula is C13H12O, 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.

General procedure: To a mixture of alcohol (1 mmol) and KBr (1.5 mmol, 0.18 g) in acetonitrile (5 mL), P2O5 (1.5 mmol, 0.23 g) was added and the reaction was stirred at room temperature for the time specified in Table 3. After reaction completion (TLC or GC), the reaction mixture was filtered and the residue washed with ethyl acetate (3 ¡Á 8 mL). The combined organic layers were washed with water (10 mL) and dried over Na2SO4. The solvent was removed under reduced pressure to afford the corresponding product. If necessary, further purification was performed by column chromatography.

The chemical industry reduces the impact on the environment during synthesis 3597-91-9, I believe this compound will play a more active role in future production and life.

Reference:
Article; Khazdooz, Leila; Zarei, Amin; Aghaei, Hamidreza; Azizi, Ghobad; Gheisari, Mohammad Mehdi; Tetrahedron Letters; vol. 57; 2; (2016); p. 168 – 171;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

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. 27129-87-9, name is (3,5-Dimethylphenyl)methanol. A new synthetic method of this compound is introduced below., 27129-87-9

Compound Ba (2.5 g, 95%) was obtained as colorless crystals using Compound A (1.8 g) obtained in Reference Example 1, 3,5-dimethylbenzyl alcohol (1.7 mL), triphenylphosphine (3.0 g), diethyl azodicarboxylate (1.8 mL) and tetrahydrofuran (7.5 mL) as described in Example 14. [0458] 1H NMR (270 MHz, CDCl3) delta6.96 (1H, brs), 6.86 (2H, brs), 4.68 (2H, s), 4.17 (2H, q), 3.89 (2H, t), 3.65 (2H, dd), 3.42 (2H, dd), 2.79 (2H, t), 2.31 (6H, s), 1.28 (3H, t).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,27129-87-9, (3,5-Dimethylphenyl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; Millennium Pharmaceuticals, Inc.; Kyowa Hakko Kogyo Co., Ltd.; US2003/225288; (2003); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

53066-19-6 , The common heterocyclic compound, 53066-19-6, name is 1-(2,6-Dichlorophenyl)ethanol, molecular formula is C8H8Cl2O, 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 -(2,6-dichlorophenyl)ethanol (9.0 g, 47.11 mmol) in THF (200 niL) at 0 C was added NaH (60% dispersion in mineral oil, 2.45 g, 61.24 mmol) inportions. When the evolution of gas bubble stopped, a solution of 3-fluoro-2-nitropyridine (6.69 g, 47.11 mmol) in THF (50 mL) was added to the system. The reaction was stirred at room temperature overnight, then quenched with H20 (10 mL) at 0 C, and concentrated in vacuo. The residue was diluted with H 0 (200 mL), and extracted with EtOAc (150 mL x 3). The combined organic phases were washed with saturated aqueous aHC03 (200 mL) followed by brine (200 mL), dried over anhydrous a2S04, filtered and concentrated in vacuo to give the title compound as a brown solid (14.34g,97.2%).

According to the analysis of related databases, 53066-19-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CALITOR SCIENCES, LLC; SUNSHINE LAKE PHARMA CO., LTD; XI, Ning; WANG, Ruyong; WANG, Liang; WO2014/89324; (2014); A1;,
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 4704-94-3, name is 2-(Hydroxymethyl)propane-1,3-diol. This compound has unique chemical properties. The synthetic route is as follows. 4704-94-3

Step a. 3-Methoxy-2-methoxymethyl-propane-1-ol Sodium hydride (60% dispersion in oil) (2.93 g, 73.2 mmol) was added to an ice-cooled solution of 2-hydroxymethyl-propane-1,3-diol (M. R. Harnden et al. J. Med. Chem. 1990, 33, 187) (3.53 g, 33.3 mmol) in DMF (100 ml) and the mixture was stirred at room temperature for 40 min. The reaction mixture was cooled with ice and iodomethane (4.56 ml, 73.2 mmol) was added, the stirring was continued allowing the mixture to reach room temperature over 24 h. The mixture was poured into ethyl acetate (300 ml) and washed with brine (150 ml). The organic phase was dried (MgSO4), and the solvent was evaporated. The crude product was purified by flash column chromatography (silica, ethyl acetate) to afford colourless oil. 1H NMR (300 MHz, CDCl3) 3.72 (2H, d), 3.47 (2H, d), 3.45 (2H, d), 3.32 (6H, s), 2.07(1H, m).

Statistics shows that 4704-94-3 is playing an increasingly important role. we look forward to future research findings about 2-(Hydroxymethyl)propane-1,3-diol.

Reference:
Patent; James Black Foundation Limited; US6479531; (2002); B1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts