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Preparation method for 3,4,5-trialkoxy phenol

A technology of methyl and ethyl, which is applied in the field of preparation 3, can solve the problems of unsuitable industrial production and low yield of phenol, and achieve the effects of avoiding reaction by-products, simplifying process steps, and achieving significant industrial application value

Active Publication Date: 2012-05-16
KPC PHARM INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] The present invention aims at the disadvantages of the low yield of 3,4,5-trialkoxyphenol prepared in the prior art and the inability to industrialize production, and provides a new preparation method, the method 3,4,5-trialkoxyphenol yield rate greater than 50%

Method used

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  • Preparation method for 3,4,5-trialkoxy phenol
  • Preparation method for 3,4,5-trialkoxy phenol
  • Preparation method for 3,4,5-trialkoxy phenol

Examples

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Effect test

Embodiment 1

[0034] Measure 35ml of dimethyl carbonate and 5ml of methanol into a 100ml reaction bottle, add 0.5g of 98% concentrated sulfuric acid and 2.1g of raw material 3,4,5-triethoxyphenyl methyl ketone successively, stir and dissolve at room temperature Then add 4ml of 30% hydrogen peroxide dropwise. The reaction mixture was stirred at room temperature for 20 hours, and then the reaction was terminated after TLC checked that the raw materials were completely reacted.

[0035] In addition, about 2.0 g of sodium sulfite was weighed and dissolved in 10 ml of water, and then slowly added to the above reaction solution, using sodium sulfite to neutralize excess hydrogen peroxide. After cooling down slightly, slowly add sodium bicarbonate solution until there is no obvious gas overflow or the pH of the aqueous phase is alkaline, about 0.84g is needed (dissolve in about 5-10ml of water and add). Because also used excessive strong acid catalysis in the reaction, adopt sodium bicarbonate to...

Embodiment 2

[0037] Measure 44ml of dimethyl carbonate and 6ml of ethanol into a 100ml reaction bottle, add 1g of 96% phosphoric acid and 1.2g of raw material 3,4,5-trimethoxybenzaldehyde successively, stir and dissolve at room temperature, then add dropwise 1.2ml of hydrogen peroxide. The reaction mixture was stirred at room temperature for 16 hours, and then the reaction was terminated after TLC checked that the raw materials were completely reacted.

[0038] Another weighed about 1.26g of sodium sulfite was dissolved in 10ml of water and slowly added to the above reaction solution. After cooling down slightly, slowly add sodium bicarbonate solution until there is no obvious gas overflow or the pH of the aqueous phase is alkaline, about 1.6g is needed. After fully stirring, 10ml of chloroform was added, and the mixture was left to stand to separate layers after continuing to stir. The organic phase was separated, and the aqueous phase was extracted once more with 15 ml of chloroform. ...

Embodiment 3

[0040] Measure 50ml of dimethyl carbonate and 5ml of methanol into a 100ml reaction bottle, add 1g of 96% sulfuric acid and 2.4g of raw material 3,4,5-triethoxybenzaldehyde successively, stir and dissolve at room temperature, then add 4.8ml dropwise of hydrogen peroxide. The reaction mixture was stirred at room temperature for 12 hours, and then the reaction was terminated after TLC checked that the raw materials were completely reacted.

[0041] Another weighed about 2.3g of sodium sulfite was dissolved in 10ml of water and slowly added to the above reaction solution. After cooling down slightly, slowly add sodium bicarbonate solution until there is no obvious gas overflow or the pH of the aqueous phase is alkaline, about 1.6g is needed. After fully stirring, add 10ml of dichloromethane, continue to stir and then let stand to separate layers. The organic phase was separated, and the aqueous phase was extracted once more with 15 ml of dichloromethane. The organic phases wer...

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Abstract

The invention relates to the field of chemical synthesis and discloses a preparation method for 3,4,5-trialkoxy phenol. According to the method, 3,4,5-trialkoxy benzaldehyde or 3,4,5-trialkoxy phenyl alkyl ketone and hydrogen peroxide are used as raw materials and are subjected to Baeyer-Villiger oxidation rearrangement reaction in a mixed solvent of dimethyl carbonate and methanol under the catalysis of a strong acid and then to basic hydrolysis, and 3,4,5-trialkoxy phenol is obtained after the strong acid is neutralized. The method provided in the invention has simple process steps, a yield of more than 50% and a remarkable application value in industrial production.

Description

technical field [0001] The invention relates to the field of chemical synthesis, in particular to a method for preparing 3,4,5-trialkoxyphenol. Background technique [0002] 3,4,5-trialkoxyphenol, its structural formula is as follows: [0003] [0004] Its synthesis often adopts 3,4,5-trialkoxybenzaldehyde or 3,4,5-trialkoxyphenyl ketone to form an intermediate ester by strong acid catalysis in the presence of peroxyacid, and then Alkaline hydrolysis forms 3,4,5-trialkoxyphenol. [0005] U.S. Patent No. 5,840,997 discloses a method for synthesizing corresponding phenols from alkoxy or aryloxy benzaldehyde. The oxidation process is a heterogeneous phase, hydrogen peroxide and formic acid are catalyzed, and methylene chloride is used as a solvent to react, and the product is obtained by alkali hydrolysis. The yield was low (1.48%), and the main by-product was the corresponding benzoic acid. [0006] The patent PCT / EP2004 / 050470 discloses that 3,4,5-trimethoxyphenyl propy...

Claims

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Application Information

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IPC IPC(8): C07C43/23C07C41/26
Inventor 张伟杨健朱海贝吴宇白奕阳陈锦锌
Owner KPC PHARM INC
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