Synthesis method for 1-chloro-1-acetyl cyclopropane

A synthesis method and technology of acetylcyclopropane, which is applied in the field of synthesis of 1-chloro-1-acetylcyclopropane, can solve the problems of difficulty in large-scale industrial production, production risk control, many raw materials, low yield, etc., and achieve improved Yield, high product purity, cost reduction effect

Inactive Publication Date: 2018-08-24
LIANYUNGANG JINDUN AGROCHEMICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In order to solve the problems in the prior art that the yield is low, many raw materials are needed, large-scale industrial production is not possible, and production risk control is difficult, the present invention provides a synthetic method of 1-chloro-1-acetylcyclopropane

Method used

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  • Synthesis method for 1-chloro-1-acetyl cyclopropane

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Add 240 g (1.2 mol) of 20% aqueous sodium hydroxide solution and 155 g of 6# solvent oil into a 1000 mL four-neck flask. Add 2.2g (0.01mol) of 15-crown-5 to the reaction system, raise the temperature of the reaction system to 25°C, add 155g (1mol) of 3,5-dichloro-2-pentanone dropwise at this temperature, and control the reaction volume at 50°C. The dropwise addition time is about 1h. After the dropwise addition, keep warm at 50°C for 1.5h. After the reaction is lowered to room temperature, separate the liquids. Wash the oil phase with 100g of water to obtain 275g of the oil phase. After drying, distill to obtain 1-chloro-1 - 110 g of acetylcyclopropane, the normalized purity detected by GC is 99%, and the calculated yield is 92.28%.

Embodiment 2

[0021] Add 400 g (2 mol) of 20% aqueous sodium hydroxide solution and 465 g of 120# solvent oil into a 1000 mL four-neck flask. Add 13.25g (0.05mol) of 18-crown-6 to the reaction system, raise the temperature of the reaction system to 80°C, add 155g (1mol) of 3,5-dichloro-2-pentanone dropwise at this temperature, and control the reaction volume at 50°C. The dropping time is about 5 hours. After the dropping is completed, keep warm at 50°C for 1.5 hours. After the reaction is cooled to room temperature, separate the liquids and wash the oil phase with 100g of water to obtain 580g of the oil phase. After drying, use GC to detect the normalized purity It was 99%, and the content of the organic layer was quantitatively analyzed, and the converted yield was 95.3%.

Embodiment 3

[0023] Add 260 g (1.3 mol) of 20% aqueous sodium hydroxide solution and 155 g of 200# solvent oil into a 1000 mL four-neck flask. Add 3.52g (0.02mol) of 12-crown-4 to the reaction system, raise the temperature of the reaction system to 25°C, add 155g (1mol) of 3,5-dichloro-2-pentanone dropwise at this temperature, and control the reaction volume at 50°C. The dropping time is about 1.5h. After the dropping, keep warm at 50°C for 1.5h. After the reaction is lowered to room temperature, separate the liquids. Wash the oil phase with 100g of water to obtain 280g of the oil phase. After drying, use GC to detect and normalize The purity is 99%, the content of the organic layer is quantitatively analyzed, and the converted yield is 94.3%.

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Abstract

The invention discloses a synthesis method for 1-chloro-1-acetyl cyclopropane. The synthesis method is characterized in that 3,5-dichloro-2-pentanone is taken as a raw material, and solvent oil is taken as a solvent to react with a 20% sodium hydroxide aqueous solution under action of a phase transfer catalyst crown ether, fluid separation and distillation can be performed to separate out 1-chloro-1-acetyl cyclopropane. Solvent oil which does not react with a system is added as the solvent, so that reaction is performed in two phases, and therefore, contact time between a product and alkalineis reduced, product purity is improved, and the yield is improved more greatly. Raw material reaction speed can be increased by adding the phase transfer catalyst, separation speed of the product anda water phase in a post-treatment process is quickened by adding the solvent, and dwell time, in the reaction system, of raw materials and product is integrally shortened, so that side reaction is reduced, and selectivity is improved.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a synthesis method of 1-chloro-1-acetylcyclopropane. Background technique [0002] Prothioconazole (prothioconazole), the chemical name is (SR)-2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-2,4- Dihydro-1,2,4-triazole-3-thione is a broad-spectrum triazole fungicide developed by Bayer. Its mechanism of action is to inhibit the precursor of sterol in fungi - lanosterol or 24-sub. Demethylation at position 14 of methyldihydrolanosterol. 1-Chloro-1-acetylcyclopropane is an important intermediate in the synthesis of the pesticide fungicide prothioconazole. [0003] Currently, there are four common synthetic methods for 1-chloro-1-acetylcyclopropane. The first method is to synthesize 1-chloro-1-acetylcyclopropane from 3-chloro-5-bromo-2-pentanone. The method has mild reaction conditions and high yield, but has the disadvantages of high raw ma...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/327C07C45/61
CPCC07C45/61C07C2601/02C07C49/327
Inventor 孙益群许高杰石卫兵孙毅
Owner LIANYUNGANG JINDUN AGROCHEMICAL CO LTD
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