A method for reducing aldehydes and ketones to alcohols

A technology of benzaldehyde and acetophenone, applied in the field of reducing aldehydes and ketones to alcohol compounds, achieving the effects of low cost, mild reaction conditions and less pollution

Inactive Publication Date: 2019-07-09
LESHAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method cannot directly convert aldehydes and ketones into alcohols, and must undergo further hydrolysis of silicon ethers to obtain alcohol compounds

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Add 10 mL of deionized water, 102 mg (0.2 mmol) tripentafluorophenylborane, and 212 mg (2.0 mmol) benzaldehyde to the reaction flask in sequence, and stir vigorously to uniformly disperse tripentafluorophenylborane and benzaldehyde in the water. Then, 216 mg (2.0 mmol) of phenylsilane was added under stirring, and stirred at room temperature for 2 hours, and benzaldehyde was reduced to benzyl alcohol. through 1 H NMR detection showed that the yield of benzyl alcohol was 100%.

[0021] The phenylsilane of this embodiment can also be replaced by equimolar silicon hydride, diphenylsilane, triphenylsilane, phenylmethylsilane, triethylsilane, diethylmethylsilane, dimethylsilane, benzyl alcohol The yield can reach 95% to 100%.

Embodiment 2

[0023] In Example 1, the benzaldehyde used was replaced with equimolar acetophenone, and other steps were the same as in Example 1, and acetophenone was reduced to 1-phenylethanol. through 1 H NMR detection showed that the yield of 1-phenylethanol was 100%.

Embodiment 3

[0025] In embodiment 1, used benzaldehyde is replaced with n-butyraldehyde of equimolarity, and other steps are identical with embodiment 1, and n-butyraldehyde is reduced to n-butanol. through 1 H NMR detection, the productive rate of n-butanol is 96%.

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PUM

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Abstract

The invention discloses a method for carrying out reduction on aldehyde and ketone to obtain alcohol. Tri-(pentafluorobenzene-base) borane is used as a catalyst, and hydrogen silane is used as a reducing agent. The method includes adding water into reaction systems and carrying out reduction on the aldehyde or the ketone under the normal-temperature condition to obtain the corresponding alcohol. Compared with the prior art, the method has the advantages that reaction can be quickly carried out under the normal-temperature and normal-pressure conditions, the reaction conditions are mild, the method is high in reaction efficiency, and the yield is 95%-100% as shown by 1H NMR (1H nuclear magnetic resonance) detection; the water can be used as a solvent used in the reaction, and accordingly the method is low in cost and little in pollution; the catalyst and the reducing agent do not contain heavy metal, and accordingly the problem of heavy metal pollution and the like can be solved by theaid of the method.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a method for reducing aldehydes and ketones to alcohol compounds under the condition of water. Background technique [0002] The research on the reduction of aldehydes and ketones to alcohols has always been one of the important research directions in organic chemistry. The reduction methods mainly include catalytic hydrogenation, metal reduction, and enzyme reduction. [0003] Catalytic hydrogenation: Most of the catalysts in this method are based on noble metals such as Ni, Pd, Pt or toxic transition metal catalytic systems. When they are used as catalysts to participate in the reduction reaction of carbonyl groups, they usually need conditions such as heating and high pressure. The reaction conditions are harsh and the requirements for equipment are relatively high. high. [0004] Metal reduction: This method uses metal hydrides to reduce aldehydes and ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07B41/02C07C29/14C07C29/143C07C33/22C07C31/12C07C41/26C07C43/23C07C33/46C07C35/08C07C201/12C07C205/19C07C35/32
CPCC07B41/02C07C29/14C07C29/143C07C41/26C07C201/12C07C2601/14C07C2602/08C07C33/22C07C31/12C07C43/23C07C33/46C07C35/08C07C205/19C07C35/32
Inventor 孙国峰聂万丽田冲鲍尔佐夫·马克西姆徐鑫王鹏
Owner LESHAN NORMAL UNIV
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