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The preparation method of trinexapac-ethyl

A technology of trinexapac-ethyl and ethyl dioxetate, applied in the field of preparation of trinexapac-ethyl, can solve the problems of low yield, increased cost, unfavorable environmental protection and the like, and achieves simple process, high yield and low cost. Effect

Inactive Publication Date: 2011-12-28
MAX RUDONG CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] In method one, the hydrogen pressure when reducing 3,5-dihydroxybenzoic acid to 3,5-cyclohexanedione-1-carboxylic acid needs to exceed 90 atmospheres, and the yield is also low. In method two, metal cyanides are highly toxic product, which is not conducive to environmental protection. Both method one and method two involve the reaction of cyclopropanyl chloride with the intermediate cyclohexanedione and then rearrangement reaction. Although method three is completed in one step, there is a molecule of cyclopropanecarboxylic acid It is not used, which increases the cost and is not suitable for industrial production

Method used

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  • The preparation method of trinexapac-ethyl

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Embodiment 1

[0018] In a three-necked reaction flask equipped with a stirring motor, a condenser, and a dropping funnel, add 36.8 grams of ethyl 3,5-dioxcyclohexyl carboxylate, 17.2 grams of cyclopropanecarboxylic acid, 100 grams of chloroform, and N, N-dimethyl With 25 grams of aniline, start to drop 13.8 grams of phosphorus trichloride under cooling to 0° C. and stirring. After the dropwise addition of phosphorus trichloride, add 7 grams of 4-dimethylaminopyridine, react at 60° C. for 4 hours, and cool to 0 ℃, add 100ml of water, adjust the pH to 5-6, separate the water layer, remove chloroform and N, N-dimethylaniline, and distill under reduced pressure to obtain the target product 4-cyclopropyl (hydroxyl) methylene 3,5-diox 37 grams of ethyl cyclohexanecarboxylate is trinexapac-ethyl, the content is 96%, and the yield is 70.5%.

Embodiment 2

[0020] In a three-necked reaction flask equipped with a stirring motor, a condenser, and a dropping funnel, add 36.8 grams of ethyl 3,5-dioxcyclohexyl carboxylate, 17.2 grams of cyclopropanecarboxylic acid, 100 grams of toluene, and 25 grams of triethylamine. Add 13.8 grams of phosphorus trichloride dropwise under cooling and stirring, and the temperature rises to 30°C. After dropping the phosphorus trichloride in 1 hour, add 5 grams of 4-dimethylaminopyridine, keep the reaction at 60°C for 5 hours, and add 100 grams of water Finally, adjust the pH to 5-6, separate the water layer, remove the toluene, and distill under reduced pressure to obtain 31 g of trinexapac-ethyl, with a content of 91% and a yield of 56.0%.

Embodiment 3

[0022] In a three-necked reaction flask equipped with a stirring motor, a condenser, and a dropping funnel, add 36.8 grams of ethyl 3,5-dioxcyclohexyl carboxylate, 17.2 grams of cyclopropanecarboxylic acid, and 100 grams of N, N-dimethylaniline, Add 13.8 grams of phosphorus trichloride dropwise under cooling and stirring. After dropping the phosphorus trichloride, add 7 grams of 4-dimethylaminopyridine, keep the reaction at 60°C for 4 hours, add 100 grams of water, adjust the pH to 5-6, and separate the water layer, removed N,N-dimethylaniline, and distilled under reduced pressure to obtain 39 grams of trinexapac-ethyl, with a content of 97.5% and a yield of 75.4%.

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Abstract

The invention discloses a preparation method of trinexapac-ethyl, which comprises adding ethyl 3,5-dioxcyclohexyl carboxylate, cyclopropanecarboxylic acid, solvent and organic amine into a reactor, and adding phosphorus trichloride dropwise, and in the presence of a catalyst, The reaction was carried out under certain conditions. After the reaction was completed, the solvent was washed with water, and the trinexapac-ethyl was obtained by distillation under reduced pressure. The invention has simple process, high yield and low cost.

Description

technical field [0001] The invention relates to a preparation method of trinexapac-ethyl. Background technique [0002] Trinexapac-ethyl is a cyclohexane carboxylic acid compound, which is an excellent plant growth regulator and herbicide. Post-emergence application on cereal and canola crops can prevent crop lodging and improve harvest yield, application on turf can reduce the frequency of mowing, and application on sugarcane can promote ripening. According to literature reports: the main preparation methods of existing trinexapac-ethyl include: Method 1 (US4963745) is that 3,5-dihydroxybenzoic acid is used as starting material by catalytic hydrogenation reduction to obtain 3,5-cyclohexanedione- 1-Formic acid, through esterification to obtain 3,5-cyclohexanedione-1-ethyl carboxylate, and then react with cyclopropanecarbonyl chloride to obtain 3-cyclopropylcarbonyloxy-5-ethoxycarbonyl-2-cyclohexyl En-1-one undergoes a rearrangement reaction under the catalysis of DMAP to o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/757C07C67/343
Inventor 马发亮蔡国平吴建文金利斌濮文均
Owner MAX RUDONG CHEM
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