Month: November 2020

2050-25-1 , The common heterocyclic compound, 2050-25-1, name is 2-(2-(Benzyloxy)ethoxy)ethanol, molecular formula is C11H16O3, 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.

Under a nitrogen atmosphere, silver trifluoromethane sulfonate (19.64 g, 76.44 mmol), lithium trifluoromethane sulfonate (3.97 g, 25.48 mmol), 1-(chloromethyl)-4-fluoro- 1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (18.05 g, 50.96 mmol) and potassium fluoride (5.92 g, 101.92 mmol) were mixed.2-(2-benzyloxyethoxy)ethanol (5 g, 25.48 mmol), trimethyl(1,1,2,2,2-pentafluoroethyl)silane (14.69 g, 76.44 mmol), EtOAc (20 mL), trifluoromethylbenzene (20 mL), and 2-fluoropyridine (7.42 g, 76.44 mmol) were then added under N2 atmosphere in this order. The reaction mixture was stirred under N2 atmosphere for 60 h at 30 C then filtered through a plug of silica (eluting with EtOAc). The filtrate was collected and concentrated. The residue was purified via silica gel chromatography (PE:EtOAc = 25:1) to obtain 2-[2-(1,1,2,2,2-pentafluoroethoxy)ethoxy]ethoxymethylbenzene (2.5 g, 31% yield) as a light yellow liquid. 1H NMR (400 MHz, CDCl3) d 7.36- 7.24 (m, 5H), 4.56 (s, 2H), 4.17- 4.11 (m, 2H), 3.76- 3.72 (m, 2H), 3.71- 3.65 (m, 2H), 3.65- 3.60 (m, 2H). 19F NMR (376 MHz, CDCl3) d -90.77 (s), -86.02 (s).

According to the analysis of related databases, 2050-25-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NAVITOR PHARMACEUTICALS, INC.; SAIAH, Eddine; O’NEILL, David, John; KANG, Seong Woo Anthony; (366 pag.)WO2019/241789; (2019); A1;,
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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.110-73-6, name is 2-(Ethylamino)ethanol, molecular formula is C4H11NO, molecular weight is 89.1362, as common compound, the synthetic route is as follows.110-73-6

General procedure: To a solution of 3-formylchromone 5 (1 equiv) in 1,2-dichloroethane was added secondary amine 6a-o (1.2 equiv) and sodium triacetoxyborohydride (1.5 equiv). After stirring at room temperature for 12 h, the reaction mixture was quenched with H2O and extracted with CH2Cl2. The combined organic layers were washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash silica gel chromatography to obtained 4a-n.

Statistics shows that 110-73-6 is playing an increasingly important role. we look forward to future research findings about 2-(Ethylamino)ethanol.

Reference:
Article; Joo, Cheonik; Venkateswararao, Eeda; Lee, Ki-Cheul; Sharma, Vinay K.; Kyung, Min-Sik; Kim, Youngsoo; Jung, Sang-Hun; Bioorganic and Medicinal Chemistry; vol. 20; 19; (2012); p. 5757 – 5762;,
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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. 6214-44-4, name is (4-Ethoxyphenyl)methanol. A new synthetic method of this compound is introduced below., 6214-44-4

A mixture of benzyl alcohol (1 mmol), phenylacetonitrile (3 mmol), 0.0998 g of metal-MgO (Pd: 0.0075 mmol; Au: 0.0075 mmol; Pt: 0.0075 mmol), trifluorotoluene (1 ml) and n-dodecane (20 mul) as internal standard were placed into an autoclave. The resulting mixtures were vigorously stirred at 180 C under nitrogen, being monitored by GC.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6214-44-4, (4-Ethoxyphenyl)methanol, and friends who are interested can also refer to it.

Reference:
Article; Corma, Avelino; Rodenas, Tania; Sabater, Maria J.; Journal of Catalysis; vol. 279; 2; (2011); p. 319 – 327;,
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13826-35-2, 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 13826-35-2 as follows.

(3-Phenoxy-phenyl)-methanol (Intermediate 46, 5 g, 25 mmol) was dissolved in DCM (50 mL), cooled to 0 C, and thionyl chloride (4 ml, 50 mmol) was added dropwise followed by a drop of DMF. The reaction mixtre was stirred at room temperature for 12 h and concentrated under reduced pressure to remove solvent. To the resulting residue was added ice and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulphate, concentrated under reduced pressure and purified by column chromatography (95%, 5.2 g). NMR: 400 MHz, DMSO- d6: delta 7.36-7.43 (m, 3H), 7.13-7.20 (m, 2H), 6.95-7.07 (m, 4H), 4.73 (s, 2H).

The chemical industry reduces the impact on the environment during synthesis 13826-35-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK PATENT GMBH; SHERER, Brian; BRUGGER, Nadia; WO2015/130905; (2015); A1;,
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78-69-3, 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. 78-69-3, name is 3,7-Dimethyloctan-3-ol, molecular formula is C10H22O, 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.

Add 2g to the reaction flaskTetraacetyl substituted glucose bromine (chemical formula:), 0.38 g of tetrahydrolinalol (chemical formula:),0.73g of silver carbonate and 10mL of dichloromethane,Reacting at room temperature for 24 hours;The solvent was removed under reduced pressure.Separated by column chromatography,The eluent (a mixture of petroleum ether and ethyl acetate in a mass ratio of 5:1) was washed down with 0.80 g of a white solid.That is, tetrahydrolinalol tetraacetyl glucoside (chemical formula:).

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. 78-69-3, 3,7-Dimethyloctan-3-ol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shanghai Institute of Technology; Li Hongyi; Pan Xianhua; Chen Yu; Huo Jiyou; Yuan Hongshun; (9 pag.)CN109970826; (2019); A;,
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440-60-8, 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 440-60-8 as follows.

In a 10 mL round bottom flask, 0.99 g of pentafluorobenzyl alcohol and 2 g of diethylene glycol dimethyl ether were sequentially added.The resulting mixture was subjected to ultrasonic irradiation at 40 kHz/30 W/70 C for 30 minutes in an ultrasonic reaction apparatus. The diethylene glycol dimethyl ether was removed under reduced pressure, and recrystallized to obtain 0.89 g of pentafluorobenzoic acid in a yield of 95%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,440-60-8, its application will become more common.

Reference:
Patent; Central South University; Xiao Fang; Xiao Yuanyuan; Zeng Ming; Li Na; Yin Lirong; (15 pag.)CN108467342; (2018); A;,
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3360-41-6, Adding a certain compound to certain chemical reactions, such as: 3360-41-6, 4-Phenylbutan-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, 3360-41-6, blongs to alcohols-buliding-blocks compound.

General procedure: To 16 (0.6 g, 0.6 mmol) was added dichloromethane (5 mL) in a round-bottom flask. After 10 min, oxalyl chlorideor oxalyl bromide was added (0.6 mmol). The reaction mixture was magnetically stirred at room temperature. Uponcessation of gas evolution, 4 was added (0.5 mmol), and the reaction mixture was heated to reflux. After thereaction was complete according to TLC analysis, the mixture was cooled to room temperature and filtered. Thesolid on the funnel was washed with dichloromethane (3 ¡Á 10 mL), and the filtrate was concentrated under reducedpressure to afford the desired product 5 in an essentially pure state based on 1H and 13C NMR spectroscopicanalyses.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3360-41-6, its application will become more common.

Reference:
Article; Xia, Xuanshu; Toy, Patrick H.; Beilstein Journal of Organic Chemistry; vol. 10; (2014); p. 1397 – 1405;,
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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.

4-aminobenzyl alcohol (1 g, 8.12 mmol) was dissolved in 5 mL of 5M hydrochloric acid solution,A solution of sodium nitrite (840 mg, 12.18 mmol, dissolved in 20 mL of deionized water) was added dropwise to the solution. The mixture was added dropwise within 30 minutes. The reaction mixture was vigorously stirred in an ice-water bath.Sodium azide (2.1 g, 32.3 mmol) was added portionwise to the reaction system, and the resulting mixture was stirred at room temperature overnight. After the reaction is complete,The residue was poured into saturated NaHCO3 solution and extracted with ethyl acetate. The organic layer was washed with saturated NaCl solution, dried over anhydrous Na2SO4, filtered and concentrated.The crude product was isolated and purified by silica gel column chromatography (EA:PE=1:3, volume ratio) to give 950 mg of a yellow oily liquid in a yield of 78.0%.

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

Reference:
Patent; Peking University; Tang Xinjing; Jin Qingqing; (36 pag.)CN107365254; (2017); A;,
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6338-55-2, 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. 6338-55-2, name is 2-(2-(2-Aminoethoxy)ethoxy)ethanol, molecular formula is C6H15NO3, 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.

To a solution of SL_0160 (269 mg, 732 mumol) in MeCN (10 mL) was added 2-(2-(2-aminoethoxy)ethoxy)ethan-1-ol (109 mg, 732 mumol) followed by NEt3 (200 muL, 145 mumol). The resulting yellow solution was left at 22 C. for 24 hours, at which point TLC analysis indicated complete consumption of starting material. Solvent was removed in vacuo, and crude residue was purified by silica gel chromatography (0?100% EtOAc/hexanes) to provide 220 mg (80% yield) of SL_0483 as a clear oil. 1H NMR (300 MHz, DMSO-d6) delta 7.15 (t, J=5.4 Hz, 1H), 5.62 (dt, J=11.4, 5.7 Hz, 1H), 5.49 (dt, J=11.4, 6.5 Hz, 1H), 4.57-4.51 (m, 3H), 4.24 (d, J=5.7 Hz, 2H) 3.51-3.46 (m, 6H), 3.42-3.37 (m, 4H), 3.11 (q, J=5.9 Hz, 2H), 0.87 (s, 9H), 0.05 (s, 6H). MS (ESI+) calc’d for C17H35NaNO6Si+ [M+H]+ 400.21, found 400.2.

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. 6338-55-2, 2-(2-(2-Aminoethoxy)ethoxy)ethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Promega Corporation; Levin, Sergiy; Ohana, Rachel Friedman; Kirkland, Thomas; Wood, Keith V.; (117 pag.)US2016/355523; (2016); A1;,
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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. 56456-49-6

To a solution of (4-chloro-2-fluorophenyl)methanol (222mg) in MeCN (20ml) was added Mn02 (480mg). The mixture was stirred for 24h. The mixture was filtered over celite, the org. layer was dried over MgS04 and evaporated in vacuo. The crude aldehyde was used without purification in the next step. LC-MS (A): tR = 0.76min; [M+H]+: not visible.

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; ACTELION PHARMACEUTICALS LTD; BUR, Daniel; GRISOSTOMI, Corinna; KIMMERLIN, Thierry; REMEN, Lubos; SIENDT, Herve; VERCAUTEREN, Magali; WELFORD, Richard; (138 pag.)WO2016/177690; (2016); A1;,
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