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有机化学
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有机化学 ›› 2009, Vol. 29 ›› Issue (10): 1631-1636. 上一篇    下一篇

研究简报

对甲苯磺酸催化下二乙酰苯与含有羟基的苯甲醛的Aldol缩合反应

罗华玲a   杨 伟a   李 颖a   曾鸿耀b   尹述凡   

  1. (a四川大学化学学院 成都 610064) (b中国科学院成都生物研究所 成都 610064)
  • 收稿日期:2008-11-23 修回日期:2009-03-19 发布日期:2009-05-05

Aldol Condensation of Diacetybenzene with Benzaldehyde Contain-ing a Hydroxyl Group Catalyzed by p-Toluenesulfonic Acid

Luo, Hualinga   Yang, Weia   Li, Yinga   Zeng, Hongyaob   Yin, Shufan*,a   

  1. (a College of Chemistry, Sichuan University, Chengdu 610064) (b Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041)
  • Received:2008-11-23 Revised:2009-03-19 Published:2009-05-05

PDF

1589

被引次数

4

以对甲苯磺酸(p-TsOH)作催化剂, 二乙酰苯与含有羟基的苯甲醛发生aldol缩合反应, 合成了3个1,3-双[3-(取代苯基)丙烯酰基]苯衍生物1～3, 3个1,4-双[3-(取代苯基)丙烯酰基]苯衍生物4～6和2个中间体7, 8, 中间体7, 8再与含有羟基的苯甲醛发生aldol反应合成了3个1-[3-(4-羟基苯基)丙烯酰基]-4-[3-(取代苯基)丙烯酰基]苯衍生物9～11, 反应均能在2～6 d内完成, 操作和后处理简便. 以上11个新化合物均未见报道, 其结构经1H NMR, IR, MS和HRMS加以确证.

关键词: p-TsOH, 二乙酰苯, 羟基苯甲醛, aldol反应

Using p-toluenesulfonic acid (p-TsOH) as a catalyst, three 1,3-bis[3-(substituted phenyl) acryloyl]benzene derivatives 1～3, three 1,4-bis[3-(substituted phenyl)acryloyl]benzene derivatives 4～6 and two intermediate compounds 7, 8 were synthesized by cross aldol condensations of diacetybenzene with benzaldehyde containing a hydroxyl group. Three 1-[3-(4-hydroxy-phenyl)acryloyl]-4-[3-(substituted phenyl)acryloyl]benzene derivatives 9～11 were obtained by aldol condensations of intermediate com-pounds 7, 8 with benzaldehyde containing a hydroxyl group. The method was very convenient, and the reac-tion time was for 2～6 d. The structures of all new compounds were characterized by 1H NMR, IR, and HRMS techniques.

Key words: p-TsOH, diacetybenzene, hydroxy benzaldehyde, aldol reaction