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Method for preparing calcium3-oxido-5-oxo-4-propionyl cyclohex-3-enecarboxylate

A technology of propionyl cyclohexane carboxylate calcium and propionyl cyclohexane carboxylate ethyl ester, applied in the field of preparation of 3,5-dioxo-4-propionyl cyclohexane carboxylate calcium

Active Publication Date: 2014-11-12
JIANGXI AGRICULTURAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] The object of the present invention is to provide a kind of calcium 3,5-dioxo-4-propionyl cyclohexanecarboxylate with low preparation cost and suitable for industrialized production A preparation method, which solves the problems of high preparation cost and difficulty in industrial production in the prior art

Method used

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  • Method for preparing calcium3-oxido-5-oxo-4-propionyl cyclohex-3-enecarboxylate
  • Method for preparing calcium3-oxido-5-oxo-4-propionyl cyclohex-3-enecarboxylate

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Embodiment 1

[0030] Diethyl maleate (500.00 g, 2.91 mol), acetone (253.00 g, 4.37 mol) and diethylamine (21.24 g, 0.291 mol) were placed in a 2 L autoclave and reacted at 150 °C for 24 h, recycle the acetone solvent to obtain the product 1 ： Diethyl acetonyl succinate. Transfer diethyl acetonyl succinate to a three-necked round-bottomed flask and add ethanol (520 mL), add sodium ethoxide ethanol solution (1 mol / L, 2.49 mol) dropwise under mechanical stirring and control the reaction temperature After the dropwise addition is completed, continue to stir at 5 °C for 2 h, then rise to room temperature and stir for 12 h; after the solution is cooled below 5 °C, add a certain amount of glacial acetic acid to neutralize the reaction solution, and recover ethanol under reduced pressure , to get the product 2 ： Ethyl 3,5-dioxocyclohexanecarboxylate. Add 1,2-dichloroethane (5 L) to a reaction vessel containing ethyl 3,5-dioxocyclohexanecarboxylate, and add propionyl chloride (204.29 g, 2.17 mol)...

Embodiment 2

[0032] Diethyl maleate (500.00 g, 2.91 mol), acetone (253.00 g, 4.37 mol) and diethylamine (21.24 g, 0.291 mol) were placed in a 2 L autoclave and reacted at 150 °C for 28 h, recycle the acetone solvent to obtain the product 1 ： Diethyl acetonyl succinate. Transfer diethyl acetonyl succinate to a three-necked round-bottomed flask and add ethanol (520 mL), add sodium ethoxide ethanol solution (1 mol / L, 2.49 mol) dropwise under mechanical stirring and control the reaction temperature After the dropwise addition is completed, continue to stir at 5 °C for 2 h, then rise to room temperature and stir for 12 h; after the solution is cooled below 5 °C, add a certain amount of glacial acetic acid to neutralize the reaction solution, and recover ethanol under reduced pressure , to get the product 2 ： Ethyl 3,5-dioxocyclohexanecarboxylate. Add 1,2-dichloroethane (5 L) into a reaction vessel containing ethyl 3,5-dioxocyclohexanecarboxylate, and add propionyl chloride (204.29 g, 2.17 mo...

Embodiment 3

[0034]Diethyl maleate (500.00 g, 2.91 mol), acetone (253.00 g, 4.37 mol) and diethylamine (21.24 g, 0.291 mol) were placed in a 2 L autoclave and reacted at 150 °C for 32 h, recycle the acetone solvent to obtain the product 1 ： Diethyl acetonyl succinate. Transfer diethyl acetonyl succinate to a three-necked round-bottomed flask and add ethanol (520 mL), add sodium ethoxide ethanol solution (1 mol / L, 2.49 mol) dropwise under mechanical stirring and control the reaction temperature After the dropwise addition is completed, continue to stir at 5 °C for 2 h, then rise to room temperature and stir for 12 h; after the solution is cooled below 5 °C, add a certain amount of glacial acetic acid to neutralize the reaction solution, and recover ethanol under reduced pressure , to get the product 2 ： Ethyl 3,5-dioxocyclohexanecarboxylate. Add 1,2-dichloroethane (5 L) to a reaction vessel containing ethyl 3,5-dioxocyclohexanecarboxylate, and add propionyl chloride (204.29 g, 2.17 mol) ...

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Abstract

The invention discloses a method for preparing calcium3-oxido-5-oxo-4-propionyl cyclohex-3-enecarboxylate. According to the method for preparing calcium3-oxido-5-oxo-4-propionyl cyclohex-3-enecarboxylate, diethyl maleate and acetone are used as raw materials, Michael addition is conducted under the catalytic action of diethylamine, Claisen condensation is conducted under the action of organic alkali, after acidification is conducted through an organic acid or a mineral acid of a non-aqueous solvent or phenols having acidity, 5-Carboxycyclohexane-1,3-dione is obtained, acylation, rearrangement, hydrolysis and a salt forming reaction are conducted under the action of acid-binding agent, and then the target product, prohexadione-calcium, can be obtained. According to the method for preparing calcium3-oxido-5-oxo-4-propionyl cyclohex-3-enecarboxylate, six steps of reactions are completed in a one-pot mode, and the problem that waste water, waste residues and the like generated in the reaction process of each step pollute the environment is solved. The preparation method of calcium3-oxido-5-oxo-4-propionyl cyclohex-3-enecarboxylate has the advantages that operation is easy, column chromatography chromatograph is not needed, the preparation cost is low, environmental friendliness is achieved, and the preparation method is suitable for industrial production.

Description

technical field [0001] The invention relates to the field of organic pesticide chemistry, in particular to a preparation method of calcium 3,5-dioxo-4-propionylcyclohexanecarboxylate. Background technique [0002] Calcium3-oxido-5-oxo-4-propionyl cyclohex-3-enecarboxylate, commonly known as calcium prohexadione, is a plant growth regulator . Its structural formula is shown in formula I as follows: [0003] [0004] At present, among the synthesis routes of prohexadione calcium reported in the literature, the route described in EP123001 has the prospect of industrialization. This document uses diethyl maleate as the starting material to prepare prohexadione calcium through six steps of Michale addition, Claisen condensation, acylation reaction, rearrangement, hydrolysis, and salt formation. The synthetic route is as follows The formula shows: [0005] [0006] However, the route reported in the literature uses column chromatography to purify the products in each ste...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C62/38C07C51/41
CPCC07C51/412C07C67/31C07C67/347C07C2601/16C07C62/38C07C69/757
Inventor 黄建平
Owner JIANGXI AGRICULTURAL UNIVERSITY
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