Month: October 2020

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

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

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

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

1. 2.3 g (0.0100 mol) of 4-trifluoromethyl-7-hydroxycoumarin (a-1) was taken in a round bottom flask, followed by the addition of 3.5g (0.025mol) of K2CO3, 0.33g (0 ? 001mol) of tetrabutylammonium br omide, and 30mL of acetone, the mixture is mixed under magnetic stirring, then 0.02 g KI was added as a catalyst;2. The mixed solution was heated at 60¡ãC under stirring, after 15 min 1.3 mL (0,015 mol) allyl bromide was added, then stirred and refluxed for 6h, TCL monitered the progress of the reaction3. After the reaction is completed, the insoluble matter such as potassium carbonate is removed by filtration and concentrated by rotary evaporation to obtain a crude product b-1, which is recrystallized from ethanol / water to give compound b-1,4-trifluoromethyl-7-allyloxy Lutein

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, 575-03-1, 7-Hydroxy-4-(trifluoromethyl)coumarin.

Reference:
Patent; (19 pag.)CN107674055; (2018); A;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

6214-44-4, 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. 6214-44-4, name is (4-Ethoxyphenyl)methanol. This compound has unique chemical properties. The synthetic route is as follows.

Take 152kg of 4-ethoxybenzyl alcohol, dissolve it in 300kg of ethyl acetate, add 212kg of 4-bromoacetanilide, add 40kg of HF in batches under ice bath, add in 60min, continue the reaction in ice bath for 30min, then heat the system. After refluxing for 7h, after the reaction is completed, it is cooled to room temperature, and the pH of the system is adjusted to 8-9 by 1mol/L sodium hydroxide solution. The organic layer is washed with saturated brine, washed with water until neutral, dried with anhydrous sodium sulfate, filtered, and the filtrate is reduced. The solvent was recovered by pressure, and 70% ethanol was crystallized to obtain 315 kg of yellow crystals, yield 91%.

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; Southeast University; Chen Junqing; Zhang Xiaolu; (9 pag.)CN108084130; (2019); B;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

623-04-1, 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. 623-04-1, name is (4-Aminophenyl)methanol. This compound has unique chemical properties. The synthetic route is as follows.

Compound 6 was synthesized from the corresponding aminated compound. For this a solution of 4-aminobenzyl alcohol (2.15 g, 17.5 mmol) were dissolved in THF (25 mL) and dropped into a rounded bottom flask cooled at 4 oC containing an aqueous solution of H2SO4 (4.8 mL 98%, in 60 mL of water). -Caution for preparing the H2SO4 solution slowly add concentrated acid into cooled water and not vice versa – Over the obtained acid solution of 4 amino benzyl alcohol in ice bath, a solution of NaNO2 (1.45g, 21 mmol) dissolved in water (10 mL) was added. The mixture was led to react 1 h in ice bath. Passed that time NaN3 (1.8 g, 28.9 mmol) dissolved in 5 mL water was added to the solution. The mixture was led to react overnight. Passed that time 4-azidobenzyl alcohol was collected by three liquid-liquid extraction processes using dichloromethane (100 mL). Fractions were collected dried over anhydrous Na2SO4, concentrated and purified by flash column chromatography (DCM: MetOH 19:1). Yield 84%.

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 623-04-1, (4-Aminophenyl)methanol.

Reference:
Article; Cao-Milan, Roberto; Castellanos, Laura; Gopalakrishnan, Sanjana; He, Luke D.; Huang, Rui; Landis, Ryan F.; Li, Cheng-Hsuan; Luther, David C.; Makabenta, Jessa Marie V.; Rotello, Vincent M.; Scaletti, Federica; Vachet, Richard W.; Wang, Li-Sheng; Zhang, Xianzhi; Chem; vol. 6; 5; (2020); p. 1113 – 1124;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

56456-49-6, 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. 56456-49-6, name is 4-Chloro-2-fluorobenzyl alcohol, the common compound, a new synthetic route is introduced below.

25 mg of Triphosgene was dissolved in 0.5 ml of dichloromethane, 5 mul of pyridine was added, and a solution of 20 mg of ethyl-3-(3-aminophenyl)-2-isopropoxypropanoate in dichloromethane and 50 mul of triethylamine were added under ice-cooling. After the insoluble substances had been removed by cotton plug filtration, 15 mg of 2-fluoro-4-chlorobenzyl alcohol was added. The solvent was removed under a stream of nitrogen, and the residue was dissolved in 0.6 ml of ethanol. 0.12 ml of 5N sodium hydroxide was added, followed by stirring at room temperature for 1 hour. The reaction solution was treated with 1 ml of water and 0.14 ml of 5N hydrochloric acid, then extracted with ethyl acetate. The organic layers were collected, and the solvent was removed under a stream of nitrogen. The residue was purified by reverse-phase HPLC using a water-acetonitrile-trifluoroacetic acid solvent system, to give 1.4 mg of the title compound. MS m/e(ESI) 438 (MNa+)

Statistics shows that 56456-49-6 is playing an increasingly important role. we look forward to future research findings about 4-Chloro-2-fluorobenzyl alcohol.

Reference:
Patent; Eisai Co., Ltd.; EP1380562; (2004); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

111-90-0, 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. 111-90-0, name is Diethylene Glycol Monoethyl Ether, the common compound, a new synthetic route is introduced below.

General procedure: TMSOTf (336 mg, 1.51 mmol) is added to a solution of the alcohol (0.755 mmol) in the respective nitrile (3 mL) and the mixture is stirred at rt for 65 h. H2O (25 mL) and brine (25 mL) are added, and the mixture is extracted with EtOAc (3 ¡Á 30 mL). The combined organic layers are dried (Na2SO4) and concentrated. The crude product is purified by flash column chromatography (silica gel).

Statistics shows that 111-90-0 is playing an increasingly important role. we look forward to future research findings about Diethylene Glycol Monoethyl Ether.

Reference:
Article; Pfaff, Dominik; Nemecek, Gregor; Podlech, Joachim; Beilstein Journal of Organic Chemistry; vol. 9; (2013); p. 1572 – 1577;,
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 702-23-8 as follows., 702-23-8

In a three-neckflask, 2-(4-methoxyphenyl)ethanol (2a, 3.00 g, 1 eq.) andtriphenylphosphine (6.72 g, 1.3 eq.) were dissolved in dryCH2Cl2 (25 ml). In an addition funnel, carbon tetrabromide(8.50 g, 1.3 eq.) was dissolved in dry CH2Cl2 (15 ml) andadded dropwise under inert atmosphere at 0 C until theaddition was complete. The reaction was allowed to stirat room temperature for an additional 4 h, or until completedisappearance of starting materials from thin-layerchromatography (TLC). The solvent was removed underreduced pressure, and the residue was purified by column chromatography using hexane and EtOAc to yield 3a as aclear oil. Yield: 4.11 g (97 %). 1H NMR (CDCl3) delta (ppm):3.08-3.12 (t, 2H), 3.51-3.55 (t, 2H), 3.79 (s, 3H), 6.85-6.87 (d, 2H), 7.12-7.14 (d, 2H).

The chemical industry reduces the impact on the environment during synthesis 702-23-8, I believe this compound will play a more active role in future production and life.

Reference:
Article; Do, Quang; Nguyen, Giang T.; Phillips, Robert S.; Amino Acids; vol. 48; 9; (2016); p. 2243 – 2251;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

100-37-8, 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. 100-37-8, name is 2-(Diethylamino)ethanol. A new synthetic method of this compound is introduced below.

General procedure: To tetrahydrofuran (THF) (1 mL) in a microwave reaction vessel were added cyclopentanol (0.067 mL, 0.74 mmol) and NaH (0.040 g, 1.68 mmol). After the reaction mixture was stirred at room temperature for 10 min, 2,6-dichloropyrazine (0.10 g, 0.67 mmol) was added and the resulting reaction mixture was heated in the microwave reactor at power 100 W and 50 C for 10 min. After removal of solvent in vacuo, the residue was treated with ethyl acetate and water mixture. Organic layer was collected and dried over anhydrous sodium sulfate. Removal of solvent in vacuo gave 2-chloro-6-(cyclopentyloxy)pyrazine 0.148 g in quantitative yield;

At the same time, in my other blogs, there are other synthetic methods of this type of compound,100-37-8, 2-(Diethylamino)ethanol, and friends who are interested can also refer to it.

Reference:
Article; Lee, Jinho; Park, Jongseong; Hong, Victor Sukbong; Chemical and Pharmaceutical Bulletin; vol. 62; 9; (2014); p. 906 – 914;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts