Method for catalyzing etherification of benzyl alcohol compounds

A technology for catalyzing benzyl alcohol and compounds, which is applied in the dehydration of hydroxyl-containing compounds to prepare ether, ether preparation, organic chemistry, etc., can solve the problem of high cost of chemical pollution, and achieve the effects of high reaction efficiency, high chemical selectivity, and simple operation

Inactive Publication Date: 2018-11-06
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

These two types of reactions will produce a lot of chemical pollution and high cost

Method used

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  • Method for catalyzing etherification of benzyl alcohol compounds
  • Method for catalyzing etherification of benzyl alcohol compounds
  • Method for catalyzing etherification of benzyl alcohol compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030]

[0031] Put benzhydryl alcohol (36.8 mg) in a 10 ml reaction tube, add 1 ml of 1,2-dichloroethane as a solvent, then add 11 mg of tripentafluorophenylborane and benzyl alcohol (43.2 mg), and the reaction temperature Raise to 60°C, react for 4 hours, then cool the reaction to room temperature, then remove the solvent and separate the product by column chromatography: benzhydryl benzyl ether 52 mg, 95% yield, colorless liquid. analyze data: 1 H NMR (400MHz, Chloroform-d) δ7.55–6.85 (m, 15H), 5.44 (s, 1H), 4.54 (s, 2H). 13 C NMR(100MHz,Chloroform-d)δ142.16,138.41,128.42,128.38,127.72,127.55,127.48,127.15,82.49,70.52.HRMS(ESI)m / z[M+Na] + :Calcd forC20H18ONa:297.1255.Found:297.1253.

Embodiment 2

[0033]

[0034] 1-phenylethanol (24.4mg) was placed in a 10ml reaction tube, 1ml of 1,2-dichloroethane was added as a solvent, followed by 11mg of tripentafluorophenylborane and benzyl alcohol (43.2mg), The reaction temperature was raised to 60°C. After 12 hours of reaction, the reaction was cooled to room temperature and the solvent was removed and the product was isolated by column chromatography: 1-phenethyl benzyl ether 40.7 mg, 96% yield, colorless liquid. analyze data: 1 H NMR (400MHz, Chloroform-d) δ7.35 (d, J = 4.4Hz, 4H), 7.29 (m, 6H), 4.57–4.39 (m, 2H), 4.29 (d, J = 11.9Hz, 1H) ,1.48(d,J=6.5Hz,3H). 13 C NMR (100MHz, Chloroform-d) δ143.78, 138.70, 128.55, 128.40, 127.74, 127.55, 127.51, 126.39, 77.28, 70.36, 24.27. HRMS (ESI) m / z [M+Na] + :Calcd for C15H16ONa:235.1099.Found:235.1098.

Embodiment 3

[0036]

[0037] Benzyl alcohol (36.8 mg) was placed in a 10 ml reaction tube, 1 ml of 1,2-dichloroethane was added as a solvent, followed by 11 mg of tripentafluorophenylborane and isopropanol (24.6 mg), and the reaction The temperature was raised to 60°C, and after 4 hours of reaction, the reaction was cooled to room temperature and the solvent was removed and the product was isolated by column chromatography: benzyl alcohol isopropyl ether 43.4 mg, 96% yield, colorless liquid. analyze data: 1 H NMR (400MHz, Chloroform-d) δ7.21(m,10H),5.40(s,1H),3.58(dt,J=12.2,6.1Hz,1H),1.13(d,J=6.1Hz,6H) . 13 C NMR (100MHz, Chloroform-d) δ143.04, 128.37, 127.30, 127.14, 80.52, 69.15, 22.33. HRMS (ESI) m / z [M+Na] + :Calcd for C16H18ONa:249.1255.Found:249.1253.

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Abstract

The invention belongs to the field of organic synthesis and discloses a method for catalyzing the etherification of benzyl alcohol compounds. The benzyl alcohol compounds are mixed with an alcohol compound A, and a solvent and tripentafluorophenylborane serving as a catalyst are added for a reaction at 60-120 DEG C for 4-6 hours to obtain benzyl alcohol etherified products; the alcohol compound Ais shown in the description, and R3 and R4 are aryl groups or alkyl groups or hydrogen atoms. In the reaction, tripentafluorophenylborane is utilized as the catalyst to achieve a dehydration etherification reaction for a series of benzyl alcohols, different alcohols can be subjected to mutually cross coupling to obtain ethers in the reaction, the same type of alcohol compounds can also be dehydrated by themselves to obtain ethers, and a stable and fast route is provided for synthesis of ether compounds. According to the method, the operation is simple, the reaction is highly efficient, and noother pollution is caused.

Description

technical field [0001] The invention is a new method for synthesizing organic compounds, specifically relating to the use of a non-metallic Lewis acid catalyst to catalyze the etherification reaction of alcohol compounds and to utilize it in the synthesis of various ether compounds. Background technique [0002] Dehydration of alcohols to form ethers is the most direct method for the synthesis of ethers. Alcohols have a wide range of sources and stable chemical properties. Therefore, the synthesis of organic ethers through alcohol dehydration has always been an important link in industrial production. [0003] Traditionally, organic ethers are synthesized from alcohols in two ways: (1) by Williamson reaction; (2) by strong acid dehydration etherification. These two types of reactions will produce a large amount of chemical pollution and high cost. It is an economical and green way to realize alcohol dehydration etherification by catalytic means. [0004] In 2015, Hu Xingen...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C41/09C07C43/164
CPCC07C41/09C07C43/164
Inventor 陈新滋孟山水
Owner SUN YAT SEN UNIV
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