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有机化学
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有机化学 ›› 2005, Vol. 25 ›› Issue (11): 1482-1486. 上一篇    下一篇

研究简报

离子液体介质中FeCl3•6H2O催化下芳香醛与5,5-二甲基-1,3-环己二酮的缩合反应

范学森*，李艳贞，张新迎，胡雪原，王键吉   

  1. (河南师范大学化学与环境科学学院 河南省环境污染控制重点实验室 新乡 453007)
  • 收稿日期:2005-04-13 修回日期:2005-05-30 发布日期:2005-10-30
  • 通讯作者: 范学森

FeCl3•6H2O Catalyzed Con-densation of Aromatic Aldehydes with 5,5-Dimethyl-1,3-cyclohexanedione in Ionic Liquids

FAN Xue-Sen*,LI Yan-Zhen,ZHANG Xin-Ying,HU Xue-Yuan,WANG Jian-Ji   

  1. (College of Chemistry and Environmental Science, Henan Key Laboratory for Environmental Pollution Con-trol,
    Henan Normal University, Xinxiang 453007)
  • Received:2005-04-13 Revised:2005-05-30 Published:2005-10-30
  • Contact: FAN Xue-Sen

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考察了在离子液体1-正丁基-3-甲基咪唑四氟硼酸盐([bmim][BF4])介质中, 芳香醛与5,5-二甲基-1,3-环己二酮的缩合反应. 实验结果表明, 在催化量的FeCl3•6H2O存在下, 该反应可高产率地生成氧杂蒽二酮类化合物3; 而在TMSCl/FeCl3•6H2O复合催化体系的催化下, 则得到氧杂蒽二酮类化合物的开环衍生物4, 反应具有非常好的选择性. 该论文提供的方法操作简单、产率高、选择性好而且对环境友好. 在反应结束后, 所用催化剂及离子液体都很容易回收, 并能有效重复使用.

关键词: FeCl3•, 6H2O, 离子液体, 催化, 氧杂蒽二酮

The reaction of aromatic aldehydes 1 with 5,5-dimethyl-1,3-cyclohexanedione 2 was investigated by using [bmim][BF4] as a reaction medium. It was found that without additional catalyst this reaction could only be realized at elevated temperature and gave a mixture of xanthenediones 3 and their ring-opening derivatives 2,2'-arylmethylenebis-(3-hydroxy-5,5-dimethyl-2-cyclohexen-1-one) (4) in poor yields. On the other hand, when it was carried out in the presence of FeCl3•6H2O, its selectivity and efficiency could be improved significantly and compound 3 could be obtained ex-clusively with high yield under optimized reaction conditions. Further study showed that when the same re-action was carried out under the catalysis of a combination of trimethylchlorosilane and FeCl3•6H2O, compound 4, without any contamination of 3, was obtained in good yield.

Key words: 6H2O, ionic liquid, FeCl3•, catalysis, xanthenedione