Method for preparing beta-keto acid ethyl ester

A technology of ethyl keto acid and ethyl acetate is applied in the field of preparation of ethyl keto acid, can solve the problems of unsatisfactory industrialization prospects, harsh reaction conditions, difficult post-processing and the like, and achieves stable product quality and reaction process conditions. Gentle, pure effect

Inactive Publication Date: 2008-07-09
SHANGHAI CHEM REAGENT RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The technical problem that the present invention solves is to provide a kind of preparation method of ethyl β-keto acid, to overcome the shortcomings of low yield, harsh reaction conditions, difficult post-processing and unsatisfactory industrialization prospects in the prior art

Method used

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  • Method for preparing beta-keto acid ethyl ester
  • Method for preparing beta-keto acid ethyl ester
  • Method for preparing beta-keto acid ethyl ester

Examples

Experimental program
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Embodiment 1

[0022] In a 500ml three-neck flask equipped with stirring, a thermometer and a dropping funnel, add 13.6g (0.08mol) potassium monoethyl malonate and 125ml ethyl acetate respectively, and slowly add 9.5g (0.097mol) anhydrous MgCl under stirring. 2 And 28ml (0.2mol) pyridine, react at room temperature for 5 hours. Cool, control the temperature at 0-5°C, add 8ml (0.06mol) propionyl chloride dropwise within 0.5 hours, and react at 5-20°C for 10 hours. Keeping the same temperature, 118ml of 10% HCl was added, and the reaction was continued for 2 hours. The organic phase was separated, the aqueous layer was extracted twice with 100ml ethyl acetate, the organic phases were combined, washed with saturated sodium bicarbonate solution, the ethyl acetate was evaporated under reduced pressure, and the fraction at 48-50°C / 670Pa was collected to obtain 15.8 grams, Yield 66.8%, purity 99.2% (GC).

Embodiment 2

[0024] 0.06mol butyryl chloride was reacted instead of propionyl chloride, and the same method as in Example 1 was collected to obtain 26.6 grams of ethyl butyryl acetate, with a yield of 72.6% and a purity of 99.6% (GC).

Embodiment 3

[0026] 0.06mol isobutyryl chloride replaces propionyl chloride and reacts, and the method identical with embodiment 1, collects the cut of 62-64 ℃ / 670Pa, obtains ethyl isobutyryl acetate 23.8 grams, productive rate 78.2%, purity 99.5% (GC) .

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Abstract

The invention discloses a process for preparing ethyl beta-ketoacid, which utilizes potassium monoethyl malonate as raw material. The raw material is condensed with acyl chloride by the effect of magnesium chloride and pyridine and is hydrochlorinated, then, target products of the invention ethyl beta-ketoacid are obtained, and the purity reaches above 99% (GC). Compared with the prior art, the invention is moderate in conditions in the reaction process, stable in product quality, fine in purity, high in yield coefficient and safe and simple in operation, thereby the invention is suitable for commercial process.

Description

technical field [0001] The invention relates to a preparation method of ethyl β-keto acid. Background technique [0002] Ethyl β-ketoacid is an important organic chemical raw material or an important pharmaceutical intermediate, such as ethyl propionoacetate is an important intermediate for the preparation of etodolac, ethyl butyryl acetate is an important intermediate for the preparation of propylthiouracil The important intermediate of ethyl isobutyryl acetate can be used as the intermediate of synthetic drug atorvastatin, and its general structural formula is: [0003] [0004] In the prior art, Chinese Journal of Medicinal Chemistry; 2000; 276-278 reported that ethyl acetoacetate and acyl chloride generate ethyl α-acyl acetoacetate, and then further decarboxylate to obtain ethyl β-ketoacid, with a yield of 39.2% , the preparation method has low yield, harsh reaction conditions and difficult post-processing. [0005] The report of J.Org.Chem.1980,45,3545-3549 drips t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/716C07C67/313
Inventor 徐朝晖蒋旭亮
Owner SHANGHAI CHEM REAGENT RES INST
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