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Method for reducing acid into alcohol by sodium borohydride

A kind of sodium borohydride, the technology of using sodium borohydride, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry and other directions, can solve the problems of difficult industrial production, inability to reduce acid, poor selectivity, etc., and achieve easy large-scale production. The effect of industrialized production, reduced risk and good reduction effect

Active Publication Date: 2013-03-06
TIANJIN SCIPHARMACN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the selectivity of lithium aluminum hydride as a reducing agent is poor, and carboxyl groups and other functional groups are often reduced; on the other hand, lithium aluminum hydride is expensive and requires very strict anhydrous treatment of reagents, which limits its practical application. Not easy to industrialize
[0003] Sodium borohydride has low reducing activity and generally cannot reduce acids

Method used

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  • Method for reducing acid into alcohol by sodium borohydride
  • Method for reducing acid into alcohol by sodium borohydride
  • Method for reducing acid into alcohol by sodium borohydride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014]

[0015] Add 128g of cyclohexanecarboxylic acid, 500mL of water, and 10g of cetyltrimethylammonium bromide into a 1L three-necked flask, and stir at room temperature for 30min. Add 19g of sodium borohydride in batches, and cool in a water bath to control the temperature not higher than 35 degrees. After the completion, the stirring reaction was continued at room temperature for 2 h. The reaction solution was extracted with 100mL*3 ethyl acetate, the organic phases were combined, dried over anhydrous magnesium sulfate, the solvent was removed by rotary evaporation, and the residue was distilled under reduced pressure to obtain 86g of the product cyclohexylmethanol, yield: 76%. MS m / z114(M+H) + 1 H NMR (400MHz, CDCl 3 )δ: 3.39(d, 2H), 2.99(s, 1H), 1.67-1.78(m, 3H), 1.17-1.46(m, 7H), 0.92(m, 1H).

Embodiment 2

[0017]

[0018] Add 122g of benzoic acid, 450mL of water, and 15g of cetyltrimethylammonium bromide into a 1L three-necked flask, and stir at room temperature for 30min. Add 19g of sodium borohydride in batches, and cool in a water bath to control the temperature not higher than 35 degrees. After completion, the stirring reaction was continued at room temperature for 3 h. The reaction solution was extracted with 100mL*3 ethyl acetate, the organic phases were combined, dried over anhydrous magnesium sulfate, the solvent was removed by rotary evaporation, and the residue was distilled under reduced pressure to obtain 95g of benzyl alcohol with a yield of 88%. MS m / z108(M+H) + 1 H NMR (400MHz, CDCl 3 )δ: 7.23-7.29 (m, 5H), 4.52 (s, 2H), 3.36 (s, 1H).

Embodiment 3

[0020]

[0021] Add 136g of benzoic acid, 600mL of water, and 15g of cetyltrimethylammonium bromide into a 1L three-necked flask, and stir at room temperature for 1h. Add 19g of sodium borohydride in batches, and cool in a water bath to control the temperature not higher than 35 degrees. After completion, the stirring reaction was continued at room temperature for 3 h. The reaction solution was extracted with 150 mL*3 ethyl acetate, the organic phases were combined, dried over anhydrous magnesium sulfate, the solvent was removed by rotary evaporation, and the residue was distilled under reduced pressure to obtain 100 g of product 4-methylbenzyl alcohol, yield: 82%. MS m / z122(M+H) + 1 H NMR (400MHz, CDCl 3 )δ: 7.05-7.29(m, 4H), 4.58(s, 2H), 2.45(s, 3H), 2.23(s, 1H).

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PUM

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Abstract

The invention discloses a method for reducing acid into alcohol by sodium borohydride. The reaction is carried out as follows: changing a reaction solvent and adding a phase transfer catalyst to reduce the acid into the alcohol by the sodium borohydride under the constant temperature by using sodium borohydride as a reducing agent, water as a solvent and cetyl trimethyl ammonium bromide as the phase transfer catalyst. By using the water as the solvent, the using of organic solvent is avoided, the pollution is reduced, and the environment protection is realized; and meanwhile, lithium aluminium hydride is replaced by the sodium borohydride, the process is simplified, and the large-scale industrial production is easily performed. The system has a good effect on fatty acid, and also has a good reduction effect on some aromatic and heterocyclic acids.

Description

technical field [0001] The invention relates to a reduction reaction, in particular to a method for sodium borohydride to reduce acid to alcohol. Background technique [0002] Carboxylic acid reduction is one of the important reactions in organic synthesis. In organic compounds, carboxylic acid is a kind of substance that is difficult to reduce. Lithium aluminum hydride can reduce carboxylic acid to alcohol. This reduction reaction has a high yield and is the most common method for reducing carboxylic acid. However, the selectivity of lithium aluminum hydride as a reducing agent is poor, and carboxyl groups and other functional groups are often reduced; on the other hand, lithium aluminum hydride is expensive and requires very strict anhydrous treatment of reagents, which limits its practical application. Difficult for industrialized production. [0003] Sodium borohydride has low reducing activity and generally cannot reduce acids. In recent years, it has been reported t...

Claims

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Application Information

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IPC IPC(8): C07B41/02C07C29/147C07C31/135C07C33/22C07C33/20C07D277/24
Inventor 何磊
Owner TIANJIN SCIPHARMACN
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