Category: alcohols-buliding-blocks

702-82-9 , The common heterocyclic compound, 702-82-9, name is 3-Aminoadamantan-1-ol, molecular formula is C10H17NO, 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.

In a 2L three-neck flask, 116.3 g (0.6954 moL) of 3-aminoadamantanol was added.70.2 g (0.6954 moL) of triethylamine, 4.8 g (0.02891 moL) of potassium iodide and 650.0 g of acetonitrile,Heat to 75-80C with stirring.100.0 g (0.5793 moL) of (S)-1-(2-chloroacetyl chloride)pyrrolidine-2-carbonitrile (dissolved in 500.0 g of acetonitrile) are added dropwise.2h drop is completed,Stir at 75-80 C for 1 h; TLC test is complete, and the reaction system is cooled to 20-30 C.The filter cake was rinsed with 400 g acetonitrile.Combine the filtrate and remove the solvent under reduced pressure (60C, -0.09–0.1MPa) to obtain an almost white solid.Add 211.0 g of a mixed solvent of ethanol and butanone in a mass ratio of 1:1 and heat to reflux to dissolve.Cool down to 20-30C, stir and crystallize for 1h, continue cooling to -5-5C,The crystals were stirred for 1 h. Filtration, 43g of butanone at 0C, and drying under reduced pressure (60C, -0.09–0.1MPa),127.3 g of white solid powder was obtained (yield 72.4%, HPLC purity 99.10%, Ia content 0.87%),Structural confirmation,

The synthetic route of 702-82-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Yantai Wanrun Pharmaceutical Co., Ltd.; Li Zhong; Hao Yu; Sun Baojia; Lin Peisen; Xiang Longming; Liu Zhigang; (10 pag.)CN104945299; (2017); B;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Adding some certain compound to certain chemical reactions, such as: 110-73-6, name is 2-(Ethylamino)ethanol, 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 110-73-6. 110-73-6

General procedure: (A) 2-(Alkylamino)ethanol2a or 2b (6 mmol) and Et3N (1.0 ml) were added with stirring tothe solution of diferrocenylcyclopropenylium tetrafluoroborate 1 (3 mmol)in dry benzene or acetonitrile (70 ml). After stirring for 6-12 h at ~80C,the volatiles were removed in vacuo; the residue was chromatographed ona column with Al2O3 (activity III) (hexane-diethyl ether, 3 :1) to affordthe reaction products 3a,b (30-32%) and 4a,b (43-44%), respectively.(B) Following the general procedure, reaction of 1b (1 mmol) in MeCN(30 ml, 80C, 6-12 h) in the presence of Et3N (0.3 ml) with amino alcohols2a,b (1 mmol) afforded compounds 3a (62-71%) or 3b (67-74%) and4a,b (3-10%).(C) Reaction of 1b (1 mmol) in dry benzene (30 ml, 80C, 6-12 h) inthe presence of Et3N (0.3 ml) with amino alcohols 2a,b (3 mmol) affordedcompounds 3a,b (5-7%) and 4a (58-77%), 4b (61-80%)

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 110-73-6.

Reference:
Article; Sanchez Garcia, Jessica J.; Flores-Alamo, Marcos; Chirinos Flores, Denis E.; Klimova, Elena I.; Mendeleev Communications; vol. 27; 1; (2017); p. 26 – 28;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

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

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 517-21-5 as follows., 517-21-5

Glyoxal sodium bisulphite hydrate (10.0 g) in water (80 ml) was warmed to 60 C. then a solution of 2,3-diaminoanisole (3.40 g) in ethanol (40 ml) was added. The stirred mixture was then heated to 80 C. for 1 h before addition of concentrated hydrochloric acid (6 drops). Heating was continued for 1 h. It was allowed to cool overnight, concentrated in vacuo and poured into aqueous potassium carbonate (40 ml). Ethyl acetate (3¡Á100 ml) extracts were washed with water (100 ml) and saturated brine (50 ml) then dried over anhydrous magnesium sulphate, filtered and evaporated in vacuo to afford the title compound as a yellow solid (3.07 g). TLC Rf 0.40 (ethyl acetate)

The chemical industry reduces the impact on the environment during synthesis 517-21-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Darwin Discovery, Ltd.; US6353010; (2002); B1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

24034-73-9, Adding a certain compound to certain chemical reactions, such as: 24034-73-9, (2E,6E,10E)-3,7,11,15-Tetramethylhexadeca-2,6,10,14-tetraen-1-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, 24034-73-9, blongs to alcohols-buliding-blocks compound.

Error Objects cannot be created from editing field codes. [0306] Ethyl 2E,6E,10E-geranylgeranyl carbamate (7a) (R= Ethyl-): A dry reaction flask equipped with a stir bar, 2 inlet was charged with alcohol 1 (0.060 g, 0.2 mmol), pyridine (0.032 mL, 0.4 m mol) and DCM (2 m L). After cooling it to 0 C, ethyl isocyanate was added dropwise and the resulting reaction mixture was allowed to stir for 24 h. The reaction was monitored by TLC. After completion of the reaction, it was quenched with H20 (5 mL), acidified, extracted with n-hexanes (3 x 15 mL) and the combined n-hexanes were washed with H20 (10 mL). After drying the organic solution over anhydrous a2S04, the solvent was evaporated and the resulting residue was purified by silica gel column chromatography using 1-2% EtOAc in n-hexanes to afford the desired carbamate 7a. Yield: 0.039g (54%); TLC f: 0.30 (10% EtOAc/n-Hexanes); LCMS: MS (m/z): 384 (M + IMa); ret. time: 14.39 min. [0307] The following carbamates 7b to 7z were prepared according to the procedu re that was used to prepare carbamate 7a.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,24034-73-9, its application will become more common.

Reference:
Patent; COYOTE PHARMACEUTICALS, INC.; SERIZAWA, Hiroaki; ARGADE, Ankush B.; DATWANI, Akash; SPENCER, Natalie; PAN, Yonghua; ERMINI, Florian; WO2013/130654; (2013); 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

Adding some certain compound to certain chemical reactions, such as: 110-73-6, name is 2-(Ethylamino)ethanol, 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 110-73-6. 110-73-6

into a 500 ml four-necked flask, 26.7 parts of 2- (ethylamino) ethanol (Tokyo Chemical Industry Co., Ltd.) 133 parts of tetrahydrofuran, 1.8 parts of 4-dimethylaminopyridine (manufactured by Tokyo Chemical Industry Co., Ltd.) 33.4 parts of triethylamine and 65.5 parts of di-tert-butyl dicarbonate (manufactured by Tokyo Chemical Industry Co., Ltd.) And refluxed for 2 hours. After cooling the reaction solution to 40 C., Dichloromethane was added to the reaction solution, The organic layer was washed with water, Washed with saturated brine, and dried over anhydrous sodium sulfate. By concentrating the organic layer under reduced pressure, 51.1 parts of an intermediate represented by the following formula (109) was obtained.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 110-73-6.

Reference:
Patent; NIPPON KAYAKU COMPANY LIMITED; MIFUJI, AKIHIRO; OHTANI, KOHEI; KAMEYA, HIROSHI; (24 pag.)JP2017/114996; (2017); A;,
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

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 162358-05-6, name is 2-(4-Octylphenyl)ethanol. This compound has unique chemical properties. The synthetic route is as follows. 162358-05-6

4-Octylphenethyl Methanesulfonate (Scheme 4). To a solution of 4-octylphenethyl alcohol (200 mg, 0.853 mmol) and triethylamine (1.19 mL, 8.53 mmol) in CH2C12 (8 mL) at 0 C was added methanesulfonyl chloride (0.33 mL, 4.27 mmol). After being stirred at rt for 5 h, the reaction mixture was evaporated, diluted with water, and the product was extracted with EtOAc. The extract was washed with brine, dried, and evaporated. Purification by silica gel chromatography, eluting with hexanes/EtOAc (5: 1), gave 253 mg (95%) of the mesylate as a yellow liquid; 1H NMR (400 MHz, CDC13) delta 0.87 (t, J = 6.9 Hz, 3H), 1.26- 1.30 (m, 10H), 1.58 (m, 2H), 2.57 (t, = 7.7 Hz, 2H), 2.83 (s, 3H), 3.02 (t, = 7.0 Hz, 2H), 4.40 (t, = 7.0 Hz, 2H), 7.14 (s, 4H); 13C NMR (100 MHz, CDC13) delta 14.1, 22.7, 29.3 (2C), 29.5, 31.6, 31.9, 35.3, 35.6, 37.3, 70.6, 128.8, 128.9, 133.4, 141.9; ESI-HRMS (M + Na)+ mlz calcd for Ci7H28Na03S 335.1657, found 335.1655.

Statistics shows that 162358-05-6 is playing an increasingly important role. we look forward to future research findings about 2-(4-Octylphenyl)ethanol.

Reference:
Patent; RESEARCH FOUNDATION OF THE CITY UNIVERSITY OF NEW YORK; UNIVERSITY OF STRATHCLYDE; BITTMAN, Robert; PYNE, Nigel J.; PYNE, Susan; BAEK, Dong Jae; LIU, Zheng; BYUN, Hoe Sup; WO2014/118556; (2014); A2;,
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