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Novel synthesis method of 1-acetyl-1-chlorocyclopropane

A synthesis method and chlorocyclopropane technology are applied in the preparation of carbon-based compounds, chemical instruments and methods, organic cyclization, etc., and can solve problems such as high cost and expensive raw materials

Pending Publication Date: 2022-05-13
LIAONING ZHONGHUI BIOTECHNOLOGY CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this method also has disadvantages such as relatively expensive raw materials and high cost.

Method used

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  • Novel synthesis method of 1-acetyl-1-chlorocyclopropane
  • Novel synthesis method of 1-acetyl-1-chlorocyclopropane
  • Novel synthesis method of 1-acetyl-1-chlorocyclopropane

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046]Add raw material 3,5-dichloro-2-pentanone (100.0g, 0.63mol) and imidazole ionic liquid 1-butyl-3-methylimidazolium bromide (1.0g) to the reaction flask, add dropwise 30% Sodium hydroxide aqueous solution (92.0g, 0.69mol), control the temperature at 30-40°C, add to complete the reaction for 1h, filter the reaction solution to remove salt, stand to separate layers, and distill the organic phase under reduced pressure to obtain the product 1-acetyl-1 - 68.5 g of chlorocyclopropane, with a purity of 96.5%, a yield of 88.5%, and the aqueous phase containing the ionic liquid can be applied mechanically.

Embodiment 2

[0048] Add raw material 3,5-dichloro-2-pentanone (100.0g, 0.63mol) and the above-mentioned aqueous phase containing ionic liquid to the reaction flask, add sodium hydroxide solid (27.8g, 0.69mol) in batches, and control the temperature At 30-40°C, the reaction was completed for 1h, the reaction solution was filtered to remove salt, and the layers were separated. The organic phase was distilled under reduced pressure to obtain 69.2g of the product 1-acetyl-1-chlorocyclopropane, with a purity of 97.1%, and a yield of 90. %, the aqueous phase containing the ionic liquid can be applied.

Embodiment 3

[0050] Add solvent dichloromethane (100g) in reaction flask, raw material 3,5-dichloro-2-pentanone (100.0g, 0.63mol) and imidazoles ionic liquid 1-butyl-3-methylimidazolium bromide ( 1.0g), add 30% sodium hydroxide aqueous solution (92.0g, 0.69mol) dropwise, control the temperature at 30-40°C, and react for 1h after addition, filter the reaction solution to remove salt, let it stand for stratification, and recover the organic phase by precipitation first The organic solvent was then distilled under reduced pressure to obtain 69.8 g of 1-acetyl-1-chlorocyclopropane with a purity of 97.3% and a yield of 90.9%. The aqueous phase containing the ionic liquid can be used mechanically.

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Abstract

The invention provides a green and efficient synthesis method of 1-acetyl-1-chlorocyclopropane, which is characterized in that under the promotion action of ionic liquid, a raw material 3, 5-dichloro-2-pentanone is subjected to closed loop under an alkaline condition to obtain the 1-acetyl-1-chlorocyclopropane. The method can be carried out in the presence or absence of other solvents, and meanwhile, the ionic liquid can be recycled and reused. Therefore, the method disclosed by the invention is green, environment-friendly and low in cost, and has a very high industrial production value.

Description

technical field [0001] The present invention relates to the field of chemical synthesis. Specifically, the novel synthesis of 1-acetyl-1-chlorocyclopropanes of the present invention. Background technique [0002] 1-acetyl-1-chlorocyclopropane is an important intermediate of the fungicide prothioconazole, and its structural formula is as follows: [0003] [0004] At present, the synthetic methods of 1-acetyl-1-chlorocyclopropane have the following categories. Wherein a kind of method is to be raw material with 3,5-dichloro-2-pentanone, under the catalysis of phase-transfer catalyst, for example crown ether (the method of CN108440267 report), halogenated tetraalkylammonium (the method of CN100579944 report) , a ring closure reaction occurs to obtain 1-acetyl-1-chlorocyclopropane. The phase transfer catalysts utilized in the above synthetic methods are expensive, resulting in high production costs. In addition, the phase-transfer catalyst utilized in the above-mentioned...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/67C07C49/327
CPCC07C45/67C07C2601/02C07C49/327C07C23/04C07C13/04C07C49/11C07B37/10C07C49/163C07C5/31Y02P20/54
Inventor 郭建法王涛韩海平孔前广方燕董建生
Owner LIAONING ZHONGHUI BIOTECHNOLOGY CO LTD
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