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3-acetoxy methyl-ethyl-2,2-dimethylcyclopropanecarboxylate synthesis method

A technology of ethyl cyclopropanyl formate and acetoxymethyl, which is applied in the field of synthesis of 3-acetoxymethyl-2,2-dimethyl-cyclopropanyl ethyl formate, can solve the problem of stirring reaction Long time, unstable product quality, complicated operation steps and other problems, to achieve the effect of shortened reaction time, stable product quality and high yield

Inactive Publication Date: 2015-06-17
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Therefore, the operation steps of this method are more complicated, and the CuOTf catalyst needs to be pre-reacted with oxazolines in benzene solution
Another key problem is that due to the batch operation in the stirred tank reactor, the stirring reaction time is long, the process safety is poor, the product quality is unstable, and the product yield is usually lower than 80%.

Method used

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  • 3-acetoxy methyl-ethyl-2,2-dimethylcyclopropanecarboxylate synthesis method

Examples

Experimental program
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Effect test

Embodiment 1

[0020] Use constant current pump 3 (Series II digital pump, Chrom Tech, Inc.) to control ethyl diazonium acetate solution 1, and use constant current pump 4 to control the output of prenyl acetate solution 2, so that the prenyl acetate solution and the The ethyl diazoacetate solution is simultaneously introduced into the inlet of the ethyl diazoacetate solution and the inlet of the prenyl acetate in the microreactor, and contacts in the microreactor to initiate the cyclopropanation reaction.

[0021] Microreactor:

[0022] CNC precision machining preparation

[0023] Material 316L stainless steel

[0024] Hydraulic diameter 0.4mm

[0025] Effective volume 230μl

[0026] Process conditions:

[0027] Ethyl diazoacetate solution (ethyl diazoacetate 71wt.%, 1,2-dichloroethane 29wt.%)

[0028] Prenyl acetate solution (prenyl acetate 97wt.%, copper complex catalyst 3wt.%)

[0029] Microreactor temperature control 110℃

[0030] reaction pressure

[0031] Prenyl acetate: ethyl...

Embodiment 2

[0039] According to the same method as in Example 1, the temperature of the microreactor was controlled to 100°C, and other experimental conditions and analysis methods were the same as those in Example 1. Implementation results: 3-acetoxymethyl-2,2-dimethyl-cyclopropane ethyl formate 69%, raw material ethyl diazoacetate 31%.

Embodiment 3

[0041] According to the same method as in Example 1, the temperature of the microreactor was controlled to 90°C, and other experimental conditions and analysis methods were the same as those in Example 1. Implementation results: 32% ethyl 3-acetoxymethyl-2,2-dimethyl-cyclopropanecarboxylate, 68% ethyl diazoacetate.

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Abstract

The invention relates to a 3-acetoxy methyl-ethyl-2,2-dimethylcyclopropanecarboxylate synthesis method, which comprises that an ethyl diazoacetate solution and an isopentenyl acetate solution are continuously pumped into a micro-reactor and react at a temperature of 80-110 DEG C, wherein the ethyl diazoacetate solution comprises (a) ethyl diazoacetate solution and (b) 1,2-dichloroethane, and the isopentenyl acetate solution comprises (c) isopentenyl acetate and (d) a copper coordination compound catalyst. According to the present invention, the copper coordination compound is innovatively adopted as the catalyst so as to accelerate the reaction, and the 1,2-dichloroethane is adopted as the solvent so as to make the reaction be performed under the homogeneous condition, such that the reaction characteristics and the micro-reactor advantages are combined through the selection of the two reagent, the synthesis method has characteristics of short reaction time, continuous process, high safety and high efficiency, and the product yield under the optimal condition can achieve 80%.

Description

technical field [0001] The invention relates to the synthesis of some key intermediates of pyrethroid insecticides, in particular to a new method for synthesizing ethyl 3-acetoxymethyl-2,2-dimethyl-cyclopropanecarboxylate. Background technique [0002] Ethyl 3-acetoxymethyl-2,2-dimethyl-cyclopropanecarboxylate is a key intermediate in the production of certain pyrethroid insecticides. The currently reported method ( stergaard N, Jensen J F, Tanner D. Tetrahedron 2001; 57: 6083-6088) is prepared by reacting ethyl diazoacetate and prenyl acetate as raw materials, dichloromethane as solvent, and CuOTf as catalyst at room temperature. Due to the large exothermic heat of the reaction, it is necessary to control the dripping speed of the raw materials, resulting in the dripping time as long as 10h. After the dropwise addition of the raw materials, it is necessary to continue stirring the reaction for 1 h. Therefore, the operation steps of this method are complicated, and the C...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/757C07C67/343
CPCC07C67/343B01J19/0093B01J31/2217B01J2231/325B01J2531/16C07C2601/02C07C69/757
Inventor 陈光文陈毅征韩梅焦凤军
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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