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Preparation method of cyclopropyl methyl ketone

A technology of cyclopropyl methyl ketone and methyl, which is applied in the field of preparation of cyclopropyl methyl ketone, can solve the problems of increased distillation and purification workload and purification cost, complex reaction method, high cost, etc., and achieves low cost and post-processing Work with simple, easy-to-control effects

Pending Publication Date: 2021-12-21
JIANGSU YUXIANG CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In the prior art, on the one hand, the raw material for the traditional production of cyclopropyl methyl ketone adopts acetyl n-propanol, which is chlorinated by adding hydrochloric acid, and then carries out ring closure reaction with alkali to obtain the organic layer cyclopropyl methyl ketone. The reaction method Complicated and costly; on the other hand, the layered solution needs to be discharged sequentially through the pipe, because the overall downward flow of the layered solution will cause partial mixing between different solutions, and then the organic layer collected by separation 5- The purity of chloro-2-pentanone is low, which increases the workload of distillation and purification and the problems of purification cost

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] A preparation method of cyclopropyl methyl ketone, which comprises:

[0021] 1) Dissolve methyl levulinate in toluene, add p-toluenesulfonic acid, add ethylene glycol under stirring, heat up and reflux for 10 h, and monitor the reaction by gas chromatography, add saturated sodium bicarbonate solution to quench the reaction; The organic phase was taken out and washed twice with water, dried over anhydrous sodium sulfate, filtered off the desiccant and concentrated under reduced pressure, the residue was 3-(2-methyl-1,3-dioxolan-2-yl ) methyl propionate;

[0022] The molar ratio of methyl levulinate, ethylene glycol and p-toluenesulfonic acid is: 1:1.05:0.15.

[0023] 2) Dissolve methyl 3-(2-methyl-1,3-dioxolan-2-yl)propionate in tetrahydrofuran, add zinc chloride, add sodium borohydride at room temperature, and complete the addition. Reflux for 4 h, add water to quench the reaction, continue to stir for 1 h, concentrate under reduced pressure to recover tetrahydrofuran...

Embodiment 2

[0033] A preparation method of cyclopropyl methyl ketone, which comprises:

[0034] 1) Dissolve methyl levulinate in toluene, add p-toluenesulfonic acid, add ethylene glycol under stirring, heat up and reflux for 11 hours, after gas chromatography monitors the reaction is complete, add saturated sodium bicarbonate solution to quench the reaction; The organic phase was washed twice with water, dried over anhydrous sodium sulfate, filtered off the desiccant and concentrated under reduced pressure, the residue was 3-(2-methyl-1,3-dioxolan-2-yl) Methyl propionate;

[0035] The molar ratio of methyl levulinate, ethylene glycol and p-toluenesulfonic acid is: 1:1.05:0.15.

[0036] 2) Dissolve methyl 3-(2-methyl-1,3-dioxolan-2-yl)propionate in tetrahydrofuran, add zinc chloride, add sodium borohydride at room temperature, and complete the addition. Reflux for 4 h, add water to quench the reaction, continue to stir for 1 h, concentrate under reduced pressure to recover tetrahydrofura...

Embodiment 3

[0046] A preparation method of cyclopropyl methyl ketone, which comprises:

[0047] 1) Dissolve methyl levulinate in toluene, add p-toluenesulfonic acid, add ethylene glycol under stirring, raise the temperature and reflux for at least 10 h, after the gas chromatography monitors the reaction is complete, add saturated sodium bicarbonate solution to quench the reaction; The organic phase was separated and washed twice with water, dried over anhydrous sodium sulfate, filtered off the desiccant and concentrated under reduced pressure, the residue was 3-(2-methyl-1,3-dioxolane-2- base) methyl propionate;

[0048] The molar ratio of methyl levulinate, ethylene glycol and p-toluenesulfonic acid is: 1:1.05:0.15.

[0049] 2) Dissolve methyl 3-(2-methyl-1,3-dioxolan-2-yl)propionate in tetrahydrofuran, add zinc chloride, add sodium borohydride at room temperature, and complete the addition. Reflux for 4 h, add water to quench the reaction, continue to stir for 1 h, concentrate under r...

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PUM

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Abstract

The invention discloses a preparation method of cyclopropyl methyl ketone. The method comprises the following steps: carrying out reflux reaction on methyl levulinate and ethylene glycol to obtain 3-(2-methyl-1, 3-dioxolane-2-yl) methyl propionate; dissolving 3-(2-methyl-1, 3-dioxolane-2-yl) methyl propionate in tetrahydrofuran, adding zinc chloride, adding sodium borohydride, and after addition, carrying out reflux reaction to obtain 3-(2-methyl-1, 3-dioxolane-2-yl) propyl-1-ol; adding a mixed aqueous solution of anhydrous zinc chloride and hydrochloric acid, and carrying out reflux reaction to obtain 5-chloro-2-pentanone; and carrying out a reaction on 5-chloro-2-pentanone and a sodium hydroxide aqueous solution at 90-95 DEG C for 0.5 h to obtain the target product cyclopropyl methyl ketone. According to the process, methyl levulinate is preferably selected as a starting raw material to prepare cyclopropyl methyl ketone, so that the raw materials are easy to obtain, the cost is low, large-scale industrial production is facilitated, in the preparation process, all steps and reaction conditions are mild and easy to control, post-treatment is simple, part of intermediates do not need to be refined and can be directly used as raw materials for next-step preparation, and the preparation process is greatly simplified.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of cyclopropyl methyl ketone. Background technique [0002] Cyclopropyl methyl ketone is an important organic raw material and intermediate. In medicine, it is mainly used in the synthesis of anti-AIDS drugs Efluviren and Ilremin. In pesticides, it is mainly used in the fungicide Azuridine Synthesis of amines and cyproconazole. [0003] In the prior art, on the one hand, the raw material for the traditional production of cyclopropyl methyl ketone adopts acetyl n-propanol, which is chlorinated by adding hydrochloric acid, and then carries out ring closure reaction with alkali to obtain the organic layer cyclopropyl methyl ketone. The reaction method Complicated and costly; on the other hand, the layered solution needs to be discharged sequentially through the pipe, because the overall downward flow of the layered solution will cause part...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/66C07C49/293C07C45/59C07C49/16C07D317/30C07D317/20
CPCC07C45/66C07C45/59C07D317/30C07D317/20C07C2601/02C07C49/16C07C49/293
Inventor 陈中兵黄剑程红伟程云涛
Owner JIANGSU YUXIANG CHEM
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