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Method for synthesizing p-hydroxyphenylglycine

A technology of p-hydroxyphenylglycine and a synthesis method, which is applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problems such as color and purity that cannot meet the requirements of splitting, complicated process operation, and increased cost, etc. Achieve the effect of low cost, simple process and high yield

Inactive Publication Date: 2011-05-11
HENAN NEWLAND PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] Synthesizing p-hydroxyphenylglycine at present is the method that adopts phenol, glyoxylic acid and ammonium salt to react directly and prepares, and its process is simple, and condition is mild, the advantage of low cost, but the highest yield of p-hydroxyphenylglycine obtained by this method can reach 60% %, color and purity cannot meet the requirements of splitting, and must be refined to reach the standard, which not only increases the cost, but also complicates the process operation

Method used

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  • Method for synthesizing p-hydroxyphenylglycine

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Embodiment 1

[0031] 247 grams of 30% glyoxylic acid is converted to 74 grams of glyoxylic acid, i.e. 1 mole; 85 grams of phenol is taken, i.e. 0.9 moles, 0.85 g of toluenesulfonic acid, and the above-mentioned phenol, glyoxylic acid, toluenesulfonic acid One-time input at 35°C, the reaction time is 20 hours; add 0.094 g of sodium bisulfite to change the color, adjust the pH to 3 with sodium hydroxide solution, control the reaction temperature at 25°C, and crystallize for 1 hour at 0°C ; The crystals were washed with a large amount of water, and then washed with the organic solvent methanol to obtain p-hydroxyphenylglycine.

[0032] It has the characteristics of simple process, low cost, high yield up to 88%, uniform color and purity, and can meet the requirements of separation.

Embodiment 2

[0034] Get 740 grams of 10% glyoxylic acid, equivalent to 74 grams of glyoxylic acid, i.e. 1 mole; get 186 grams of phenol, i.e. 2 moles, 0.0186 grams of benzenesulfonic acid, the above-mentioned phenol, glyoxylic acid, benzenesulfonic acid One-time input at 75°C, the reaction time is 5 hours; add 0.186 g of sodium sulfite to change the color, adjust the pH to 6 with ammonia solution, control the reaction temperature at 25°C, and the crystallization time is 10 hours at 40°C; Wash with water, and then rinse with organic solvent ethanol to obtain p-hydroxyphenylglycine.

[0035] It has the characteristics of simple process, low cost, high yield, uniform color and purity, and can meet the requirements of separation.

Embodiment 3

[0037] 247 grams of 30% glyoxylic acid is converted into 74 grams of glyoxylic acid, i.e. 1 mol; Add sulfonic acid at 50°C once, and the reaction time is 10 hours; add 0.186 g of hydroxylamine hydrochloride to change the color, adjust the pH to 6 with lithium hydroxide solution, control the reaction temperature at 50°C, and crystallize for 5 hours at 20°C ; The crystals were washed with a large amount of water, and then washed with the organic solvent acetone to obtain p-hydroxyphenylglycine.

[0038] It has the characteristics of simple process, low cost, high yield, uniform color and purity, and can meet the requirements of separation.

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Abstract

The invention belongs to the technical field of medicinal and chemical intermediate production, and relates to a method for synthesizing p-hydroxyphenylglycine. The method comprises the following steps of: adding catalyst in a ratio of phenol to glyoxylic acid of 0.9 to 2 at one time at the temperature of between 35 and 75 DEG C, and reacting for 5 to 20 hours; adding a small amount of reductive substance for decolorization, adjusting the pH value by using alkali, and crystallizing for 1 to 10 hours at the temperature of between 0 and 40 DEG C; and washing the crystal by using a large amount of water, and then flushing the crystal by using an organic solvent. The method has simple process and low cost, the yield can reach 60 percent, and the color and the purity cannot meet the resolution requirements.

Description

[0001] Field [0002] The field of the present invention relates to the technical field of production of pharmaceutical and chemical intermediates, and relates to a synthetic method of a compound having the following structure: [0003] [0004] Its chemical name is p-hydroxyphenylglycine (referred to as HPG), which is the side chain of semi-synthesized amoxicillin and cefadroxil, and is also used in the photosensitive field and analytical reagents such as Fe, P, and Si. Background technique [0005] Synthesizing p-hydroxyphenylglycine at present is the method that adopts phenol, glyoxylic acid and ammonium salt to react directly and prepares, and its process is simple, and condition is mild, the advantage of low cost, but the highest yield of p-hydroxyphenylglycine obtained by this method can reach 60% %, color and purity cannot meet the requirements for splitting, and must be refined to reach the standard, which not only increases the cost, but also complicates the proces...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C229/36C07C227/04
Inventor 谢建中张芦苇刘万民
Owner HENAN NEWLAND PHARMA
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