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Preparation method of 4-acetoxyl-2-methyl-2-butene-1-aldehyde

An acetoxy and methyl technology, which is applied in the field of preparation of 4-acetoxy-2-methyl-2-butene-1-aldehyde, can solve the problems of environmental pollution, poor selectivity, complicated post-processing and the like, Achieve the effect of high purity, low environmental pollution and low cost

Inactive Publication Date: 2010-09-01
ZHEJIANG MEDICINE CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The present invention mainly overcomes the problems of poor selectivity, complex post-processing and serious environmental pollution in the preparation process of 4-acetoxy-2-methyl-2-butene-1-aldehyde, and provides a high selectivity, A method for preparing 4-acetoxy-2-methyl-2-butene-1-aldehyde with mild reaction conditions, simple operation, no solid waste during the reaction, and easy purification of the product

Method used

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  • Preparation method of 4-acetoxyl-2-methyl-2-butene-1-aldehyde
  • Preparation method of 4-acetoxyl-2-methyl-2-butene-1-aldehyde

Examples

Experimental program
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Effect test

Embodiment 1

[0023] In a 100ml three-necked round-bottom flask equipped with magnetic stirring, add 14.40g (0.10mol) of 4-acetoxy-2-methyl-2-buten-1-ol and 20ml of benzotrifluoride as a solvent. Stir for 3-5min, then add THMPO 0.86g (5mmol) and Fe(NO 3 ) 3 9H 2 O 2.02g (5mmol), and slowly into the pure oxygen. Samples were taken after 3 hours of reaction, and GC analysis showed that the conversion rate of 4-acetoxy-2-methyl-2-buten-1-ol was 99.3%.

Embodiment 2

[0025] In a 100ml three-necked round-bottomed flask equipped with magnetic stirring, add 14.40g (0.10mol) of 4-acetoxy-2-methyl-2-buten-1-ol and 20ml of benzotrifluoride as a solvent. Stir for 3-5min, then add 4-O-TEMPO 0.52g (3mmol) and Fe(NO 3 ) 3 9H 2 O 1.21g (3mmol), and slowly into the pure oxygen. Samples were taken after 6 hours of reaction, and GC analysis showed that the conversion rate of 4-acetoxy-2-methyl-2-buten-1-ol was 99.6%.

Embodiment 3

[0027] In a 100ml three-necked round-bottomed flask equipped with magnetic stirring, add 14.40g (0.10mol) of 4-acetoxy-2-methyl-2-buten-1-ol and 20ml of benzotrifluoride as a solvent. Stir for 3-5min, then add 4-OCH in sequence 3 -TEMPO 0.86g (10mmol) and anhydrous Fe (NO 3 ) 3 2.02g (10mmol), and slowly into the pure oxygen. Samples were taken after 5 hours of reaction, and GC analysis showed that the conversion rate of 4-acetoxy-2-methyl-2-buten-1-ol was 98.8%.

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Abstract

The invention discloses a preparation method of 4-acetoxyl-2-methyl-2-butene-1-aldehyde, comprising the step of: carrying out catalytic oxidation on 4-acetoxyl-2-butene-1-alcohol as a raw material and pure oxygen or air as an oxidizing agent, the series compound of a tetramethyl-piperidine oxide as a main catalyst and ferric nitrate as an assistant in a solvent under the condition of a certain temperature to obtain the 4-acetoxyl-2-methyl-2-butene-1-aldehyde. The preparation method has the characteristics of high selectivity, mild reaction condition and simple operation; and solid wastes can not be generated in the reaction process, and products are easy to refine.

Description

technical field [0001] The invention relates to a preparation method of 4-acetoxy-2-methyl-2-buten-1-aldehyde used for synthesizing a pharmaceutical intermediate. Background technique [0002] 4-Acetoxy-2-methyl-2-buten-1-al, also known as five-carbon aldehyde, is one of the important intermediates for the synthesis of vitamin A. Its structural formula is as follows: [0003] [0004] US5527952 report adopts 2,2,6,6-tetramethylpiperidine oxide (TEMPO) as main catalyst, CuCl is auxiliary agent, in N,N-dimethylformamide (DMF) solution, logical oxygen is to 4 -Acetoxy group-2-methyl-2-butene-1-alcohol carries out catalytic oxidation reaction, obtains 4-acetoxy group-2-methyl-2-butene-1-aldehyde, but this method selectivity is relatively Poor, there are more side reactions, and the obtained product has a lower trans-product content. Moreover, since CuCl is used as an auxiliary agent, a large amount of solid waste will be generated in the reaction process, which will pollute...

Claims

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Application Information

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IPC IPC(8): C07C69/145C07C67/29
Inventor 梁智平胡赞喜于绪平
Owner ZHEJIANG MEDICINE CO LTD
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