Method for synthesizing 2,6-dimethyl phenoxyacetic acid

A technology of dimethylphenoxyacetic acid and a synthesis method, applied in 2 fields, can solve problems such as being unsuitable for industrial production, expensive raw materials, and large pollution, and achieve the effects of reduced reaction difficulty, easy post-processing, and short reaction time

Inactive Publication Date: 2011-02-09
厦门市亨瑞生化有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This method has the problems of expensive raw materials,

Method used

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  • Method for synthesizing 2,6-dimethyl phenoxyacetic acid
  • Method for synthesizing 2,6-dimethyl phenoxyacetic acid
  • Method for synthesizing 2,6-dimethyl phenoxyacetic acid

Examples

Experimental program
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Embodiment 1

[0029] 1. Add 12.2g (0.1mol) of 2,6-dimethylphenol into a 250ml beaker, heat up to 40°C, add 16g (0.1mol) of 25% NaOH solution, stir and dissolve, filter after fully reacting, and heat up the filtrate Water was removed at 110°C to obtain 12.4 g of solid powder of sodium 2,6-dimethylphenate.

[0030] 2. Take 12.4g (0.086mol) of sodium 2,6-dimethylphenolate and 8.127g (0.086mol) of chloroacetic acid into a 250ml dry three-necked flask, heat up to 150°C under a nitrogen atmosphere, and react at a constant temperature for 1.5 h. After the reaction is completed, wait for the reaction flask to cool down slightly, add 50ml of warm water therein, and shake it. When the solution is cooled to room temperature, the solid crude product can be obtained by filtration. The crude product was recrystallized from ethanol-water to obtain 12.6 g of pure 2,6-dimethylphenoxyacetic acid with a molar yield of 70%.

Embodiment 2

[0032] 1. Add 12.2g (0.1mol) of 2,6-dimethylphenol into a 250ml beaker, add 18g (0.135mol) of 30% NaOH solution, stir and dissolve, filter after fully reacting, and heat up the filtrate to 110°C to remove water , to obtain 13.0 g of solid powder of sodium 2,6-dimethylphenoxide.

[0033] 2. Take 13.0g (0.090mol) of 2,6-dimethylphenate sodium and 8.505g (0.090mol) of chloroacetic acid into a 250ml dry three-necked flask, heat up to 130°C under a nitrogen atmosphere, and react at a constant temperature for 1.5 h. After the reaction is completed, wait for the reaction flask to cool down slightly, add 50ml of warm water therein, and shake it. When the solution is cooled to room temperature, the solid crude product can be obtained by filtration. The crude product was recrystallized from ethanol-water to obtain 13.20 g of pure 2,6-dimethylphenoxyacetic acid with a molar yield of 73.2%.

Embodiment 3

[0035] 1. Add 12.2g (0.1mol) of 2,6-dimethylphenol into a 250ml beaker, add 6.8g (0.17mol) of NaOH and 12g of water, stir and dissolve, filter after fully reacting, and heat up the filtrate to 110°C to remove water to obtain 13.0 g of solid powder of sodium 2,6-dimethylphenate.

[0036] 2. Take 13.0g (0.090mol) of sodium 2,6-dimethylphenolate and 8.505g (0.090mol) of chloroacetic acid into a 250ml dry three-necked flask, heat up to 140°C under a nitrogen atmosphere, and react at constant temperature for 2 hours , after the reaction was completed, the reaction bottle was slightly cooled, 50 ml of 30% NaOH solution was added thereto, shaken, and when the solution was cooled to room temperature, the solid crude product could be obtained by filtration. The crude product was recrystallized from ethanol-water to obtain 13.48 g of pure 2,6-dimethylphenoxyacetic acid with a molar yield of 74.8%.

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Abstract

The invention discloses a method for synthesizing 2,6-dimethyl phenoxyacetic acid, comprising the following steps of: (1) adding 2,6-dimethyl phenol to an alkali aqueous solution, wherein the 2,6-dimethyl phenol and alkali are added in the mole ratio of 0.5-1.0:1.0; (2) stirring to dissolve the mixture, then filtering after sufficient reaction, increasing the temperature of a filtering material and dewatering to obtain 2,6-dimethyl phenolate; (3) mixing the 2,6-dimethyl phenolate and chloroacetic acid in the mole ratio of 0.5-1.0:1.0, heating till the 2,6-dimethyl phenolate and the chloroacetic acid are completely melted, and reacting in an inert gas atmosphere; (4) after the reaction is finished, cooling to room temperature, adding water or alkali liquor for washing, and filtering to obtain a crude product; and (5) recrystallizing the crude product to obtain a 2,6-dimethyl phenoxyacetic acid pure product. The synthesizing method has the advantages of simple and convenient operation, short reaction time, easy postprocessing, few side product, high productivity, and the like.

Description

technical field [0001] The invention relates to an improved synthesis method, in particular to a synthesis method of 2,6-dimethylphenoxyacetic acid. Background technique [0002] 2,6-Dimethylphenoxyacetic acid is a very important intermediate of the anti-AIDS drug lopinavir, and its structural formula is as follows: [0003] [0004] Two kinds of synthetic methods of 2,6-dimethylphenoxyacetic acid are introduced in the patent EP0876353A1: [0005] 1) It is formed by 2,6-dimethylphenol and chloroacetic acid through an ether-forming reaction, and the specific operation steps are as follows: [0006] [0007] Add 102.8 g (0.842 mol) of 2,6-dimethylphenol, 159.6 g (1.68 mol) of chloroacetic acid, and 1000 ml of water into a three-necked flask, and stir to dissolve. Slowly add 500ml of aqueous sodium hydroxide solution, then heat to reflux. Two hours later, 79.4 g (0.84 mol) of chloroacetic acid and 200 ml of sodium hydroxide solution were added. After 19 hours, 39.8 g ...

Claims

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Application Information

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IPC IPC(8): C07C51/367C07C59/70
Inventor 侯鹏翼赵雄超温兆辉巫立欣
Owner 厦门市亨瑞生化有限公司
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