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Method for synthesizing methyl 2-methyl-4-acetyl benzoate

A technology for the synthesis of methyl acetyl benzoate, which is applied to the preparation of carboxylic acid esters, chemical instruments and methods, and condensation to prepare carbonyl compounds, etc., can solve the problems of high price, highly toxic potassium cyanide, and toxic carbon monoxide, etc., and achieve The effect of high reaction yield, simple operation and low cost

Inactive Publication Date: 2019-04-02
荆门医药工业技术研究院 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the route of synthesizing the intermediate can be roughly divided into two categories: one is to generate the target product under the catalysis of metal palladium by 3-methyl-4-bromoacetophenone and carbon monoxide, but metal palladium belongs to rare metals and is expensive. And carbon monoxide is poisonous, which is not conducive to large-scale production
The second type of synthetic route obtains products by reacting 3-methyl-4-bromoacetophenone and potassium cyanide, but potassium cyanide is highly toxic and requires very strict requirements on personnel and the environment, so it is not suitable for large-scale production

Method used

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  • Method for synthesizing methyl 2-methyl-4-acetyl benzoate

Examples

Experimental program
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Effect test

Embodiment 1

[0017] Preparation of 4-fluoro-3-methylacetophenone

[0018] Add 11 grams (0.1mol) of 2-fluorotoluene, 33.4 grams (0.25mol) of aluminum trichloride, and 100ml of dichloromethane into a 250ml three-necked flask. The temperature is controlled at -5°C, and 8.6 grams (0.11 mol) Acetyl chloride, after the dropwise addition is completed, warm up to normal temperature, react for 2 hours, TLC detection, after the reaction is complete, add 50mL of ice water and 25mL of dilute hydrochloric acid at 0 ℃, separate, wash, dry, and rotary evaporate , to obtain 13.5 grams of colorless liquid, yield 88%.

[0019] Preparation of 3-methyl-4-cyanoacetophenone

[0020] Add 7.6 grams (0.05mol) of 4-fluoro-3-methylacetophenone, 21.2 grams (0.05mol) of potassium ferrocyanide, 10% tetrabutylammonium bromide, 100ml of N,N-Dimethylformamide, heat up to 140°C, react for 16 hours, TLC detection, after the reaction of the raw materials, cool down to 80°C, add 100ml of ethyl acetate, reflux for 1 hour, st...

Embodiment 2

[0026] Preparation of 4-fluoro-3-methylacetophenone:

[0027] Add 11 grams (0.1mol) of 2-fluorotoluene, 33.4 grams (0.25mol) of aluminum trichloride, and 100ml of chloroform into a 250ml three-necked flask. The temperature is controlled at -5°C, and 8.6 grams (0.11 mol) Acetyl chloride, after the dropwise addition is completed, warm up to normal temperature, react for 2 hours, TLC detection, after the reaction is complete, add 50mL of ice water and 25mL of dilute hydrochloric acid at 0 ℃, separate, wash, dry, and rotary evaporate , to obtain 14 grams of colorless liquid, yield 91%.

[0028] Preparation of 3-methyl-4-cyanoacetophenone:

[0029] Add 7.6 grams (0.05mol) of 4-fluoro-3-methylacetophenone, 21.2 grams (0.05mol) of potassium ferrocyanide, 10% tetrabutylammonium bromide, 100ml of N-methylimidazole, heat up to 160°C, react for 14 hours, TLC detection, after the reaction of the raw materials, cool down to 80°C, add 100ml of ethyl acetate, reflux for 1 hour, stop heatin...

Embodiment 3

[0035] Preparation of 4-fluoro-3-methylacetophenone

[0036] Add 11 grams (0.1mol) of 2-fluorotoluene, 16.2 grams (0.1mol) of ferric chloride, and 100ml of carbon tetrachloride into a 250ml three-necked flask. The temperature is controlled at -5°C, and 8.6 grams ( 0.11mol) of acetyl chloride, after the dropwise addition was completed, the temperature was raised to 80°C, reacted for 8 hours, and detected by TLC. After the reaction was completed, 50mL of ice water and 25mL of dilute hydrochloric acid were added at 0°C, separated, washed, and dried. Rotary evaporation gave 7.8 g of a colorless liquid with a yield of 50.7%.

[0037] Preparation of 3-methyl-4-cyanoacetophenone

[0038] Add 7.6 grams (0.05mol) of 4-fluoro-3-methylacetophenone, 21.2 grams (0.05mol) of potassium ferrocyanide, 10% tetrabutylammonium bromide, 100ml of N-butylimidazole, heat up to 140°C, react for 14 hours, TLC detection, after the reaction of the raw materials, cool down to 80°C, add 100ml of ethyl ac...

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Abstract

The invention provides a method for synthesizing methyl 2-methyl-4-acetyl benzoate. The method comprises the following steps: (1) adding an acylating reagent to a solution with dissolved 2-fluorotoluene, and carrying out an acylation reaction so as to obtain 4-fluoro-3-methylacetophenone; (2) dissolving the obtained 4-fluoro-3-methylacetophenone, adding a cyanation reagent, and carrying out a cyanation reaction so as to obtain 3-methyl-4-cyanoacetophenone; (3) adding acid to the 3-methyl-4-cyanoacetophenone, and carrying out a hydrolysis reaction so as to obtain 2-methyl-4-acetylbenzoic acid;and (4) adding methanol to the 2-methyl-4-acetylbenzoic acid, and carrying out an esterification reaction so as to obtain methyl 2-methyl-4-acetyl benzoate. The method has simple operation, a high reaction yield, easily purchasable reagents and instruments and low cost, and is feasible in specific practical application.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a synthetic method of methyl 2-methyl-4-acetylbenzoate. Background technique [0002] Methyl 2-methyl-4-acetylbenzoate is an important intermediate in the synthesis of many pesticides. At present, the route of synthesizing the intermediate can be roughly divided into two categories: one is to generate the target product under the catalysis of metal palladium by 3-methyl-4-bromoacetophenone and carbon monoxide, but metal palladium belongs to rare metals and is expensive. And carbon monoxide is poisonous, which is not conducive to large-scale production. The second type of synthetic route obtains the product by reacting 3-methyl-4-bromoacetophenone and potassium cyanide, but potassium cyanide is highly toxic and requires very strict requirements on personnel and the environment, so it is not suitable for large-scale production. [0003] Therefore, finding a suitable reaction rout...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/08C07C69/76
CPCC07C45/46C07C51/08C07C67/08C07C253/14C07C69/76C07C65/32C07C255/56C07C49/807
Inventor 毛学荣杨成雄何晓强许方亮李立威
Owner 荆门医药工业技术研究院
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