Chem. J. Chinese Universities ›› 1987, Vol. 8 ›› Issue (6): 533.

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Reaction and Synthesis of 8-Carboxyethyl ⊿9Hexahydrocoumarin

Huang Huamin, Li Yezhi, Wang Zhongren   

  1. Department of Chemistry Jilin University, Changchun
  • Received:1985-01-15 Online:1987-06-24 Published:1987-06-24

Abstract: 2,6-Di(β-cyanoethyl) cyclohexanone 1 was prepared by treating cyclohexa-none with acrylonitrile in the presence of KOH/ethyleneglycol, then 1 was converted to 2,6-di(carboxyelhyl) cyclohexanone 2 by refluxing with dil HCl. When 2 was heated in xylene with ferric sulfate 8-carboxyethyl ⊿9hexahydrocoumarin 3 was formed. 2 reacted with alcohols (ethanol, propanol, butanol, pentanol) by the action of hydrated ferric sulfate as catalyst, the esters 4,5,6 and 7 were obtained, respectively. 3 could easily be hydrolyzed, alcoholyzed and ammonolyzed to give 2,6,7 and 8. 3 reacted with bromine and then heated, hydrobromied was quickly liberated from the addition product thus 9 was formed. When a xylene solution of 9 and maleic anhydride was refluxed for 11h the adduct 10 was obtained.

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