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

Chin. J. Org. Chem. ›› 2009, Vol. 29 ›› Issue (10): 1631-1636. Previous Articles Next Articles

Notes

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

(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, Hualing^a Yang, Wei^a Li, Ying^a Zeng, Hongyao^b Yin, Shufan^*,a

(^aCollege 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

Abstract

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

Cite this article

LUO Hua-Ling, YANG Wei, LI Ying, CENG Hong-Yao, YIN Shu-Fan. Aldol Condensation of Diacetybenzene with Benzaldehyde Contain-ing a Hydroxyl Group Catalyzed by p-Toluenesulfonic Acid[J]. Chin. J. Org. Chem., 2009, 29(10): 1631-1636.

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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

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

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