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Method for synthesizing pentene dianhydride compound by using carbon dioxide

A glutacinic anhydride and carbon dioxide technology, applied in the direction of organic chemistry, can solve the problems of insufficient economic greenness, low efficiency, and long reaction steps, and achieve the effects of environmental friendliness, safe and simple operation, and low toxicity

Inactive Publication Date: 2020-05-12
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These methods need to use multi-step reactions to construct the diacid precursor in advance, and then use a dehydrating agent to form a ring. The reaction steps involved are long, the efficiency is low, the post-treatment process is cumbersome, and it is not economical and green enough.

Method used

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  • Method for synthesizing pentene dianhydride compound by using carbon dioxide
  • Method for synthesizing pentene dianhydride compound by using carbon dioxide

Examples

Experimental program
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Effect test

Embodiment 1

[0022] Add a stirring bar, 0.1 mmol of 3-phenyl-2-butenoic acid pentafluorophenyl ester, 0.3 mmol of 1,8-diazabicycloundec-7-ene into a 20 ml autoclave , 2 milliliters of acetonitrile, rushed into 1.0MPa carbon dioxide, after stirring at 25 degrees Celsius for 24 hours, slowly released unreacted carbon dioxide, and the reaction solution was rotary evaporated under reduced pressure to remove acetonitrile to obtain a crude product, which was purified by column chromatography to obtain the target product. The eluent used in column chromatography was ethyl acetate and acetic acid in a volume ratio of 100:1. The yield was 90%.

Embodiment 2

[0024] Add a stirring bar, 0.1 mmol of 3-phenyl-2-butenoic acid pentafluorophenyl ester, 0.10 mmol of 1,8-diazabicycloundec-7-ene into a 20 ml autoclave , 2 milliliters of acetonitrile, rushed into 1.0MPa carbon dioxide, after stirring at 25 degrees Celsius for 24 hours, slowly released unreacted carbon dioxide, and the reaction solution was rotary evaporated under reduced pressure to remove acetonitrile to obtain a crude product, which was purified by column chromatography to obtain the target product. The eluent used in column chromatography was ethyl acetate and acetic acid in a volume ratio of 100:10. The yield was 64%.

Embodiment 3

[0026] Add a stirring bar, 0.1 mmol of 3-phenyl-2-butenoic acid pentafluorophenyl ester, 0.3 mmol of 1,8-diazabicycloundec-7-ene into a 20 ml autoclave , 2 milliliters of acetonitrile, rushed into 0.1MPa carbon dioxide, stirred at 25 degrees Celsius for 24 hours, slowly released unreacted carbon dioxide, and the reaction liquid was rotary evaporated under reduced pressure to remove acetonitrile to obtain a crude product, which was purified by column chromatography to obtain the target product. The eluent used in column chromatography was ethyl acetate and acetic acid in a volume ratio of 100:1. The yield was 84%.

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Abstract

The invention belongs to the technical field of fine chemical synthesis, and relates to a method for synthesizing a pentene dianhydride compound by using carbon dioxide. The method comprises the following steps: using a 2-butenoic acid derivative as a raw material; adding an organic alkali and a reaction solvent, introducing carbon dioxide, stirring at 0-50 DEG C to react for 0.5-24 hours, standing to room temperature after the reaction is finished, slowly releasing unreacted gas, directly concentrating the reaction solution under reduced pressure to obtain a crude product, and carrying out column chromatography or recrystallization purification to obtain the pentene dianhydride product. According to the method, the 2-butenoic acid derivative and carbon dioxide which are cheap and easily available are used as raw materials, organic alkali is used as an accelerant, and the method is safe and simple to operate, low in toxicity and environment-friendly and has potential application valuein fine organic synthesis of medicines, pesticides and the like.

Description

technical field [0001] The invention belongs to the technical field of fine chemical synthesis, and relates to a method for synthesizing glutaconic anhydride compounds with carbon dioxide. Background technique [0002] Gluconedic anhydrides are an important class of organic synthesis intermediates and potential alkylene oxide comonomers, which are widely used in the synthesis of glutaconic acid derivatives and the construction of oxygen-containing heterocyclic compounds through cycloaddition reactions. [0003] The traditional synthesis method of glutaconedic anhydrides mainly relies on the dehydration reaction of glutaconedic acid compounds etc. .Kita, K.Higuchi, Y.Yoshida, K.Iio, S.Kitagaki, K.Ueda, S.Akai and H. Fujioka, J.Am.Chem.Soc., 2001, 123, 3214; (c)J .Song, Y.-X.Lei and Z.Rappoport, J.Org.Chem., 2007, 72, 9152; (d) C.T.Mbofana and S.J.Miller, J.Am.Chem.Soc., 2014, 136, 3285 ; (e) G. Zhao, J. Wu, W.-M. Dai, Tetrahedron, 2015, 71, 4779; (f) Y. Cao, X. Zhang, G. Li...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D309/36C07D407/04
CPCC07D309/36C07D407/04
Inventor 张文珍张珂张敏任伟民吕小兵
Owner DALIAN UNIV OF TECH
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