高等学校化学学报

高等学校化学学报 ›› 1987, Vol. 8 ›› Issue (6): 533.

• 论文 • 上一篇    下一篇

8-羧乙基⊿9六氢香豆素的合成及其反应

黄化民, 李叶芝, 王忠仁   

  1. 吉林大学化学系
  • 收稿日期:1985-01-15 出版日期:1987-06-24 发布日期:1987-06-24

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

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摘要： 环己酮与丙烯腈在氮氧化钾的乙二醇饱和溶液催化下合成了2,6-二(氰乙基)环己酮1,1水解得2,6-二(羧乙基)环己酮2经固体硫酸铁水合物催化加热合成了8-羧乙基⊿9六氢香豆素3.2与乙醇、丙醇、丁醇、戊醇在硫酸铁水合物催化下反应得相应的二元酸酯4、5、6及7。

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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