Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (4): 1062-1067.DOI: 10.6023/cjoc201908014 Previous Articles     Next Articles


张静静a,b, 姚明b, 李立a,b, 桑大永b, 熊航行a,b, 刘生鹏a   

  1. a 武汉工程大学化工与制药学院 武汉 430205;
    b 荆楚理工学院化工与药学院 荆门 448000
  • 收稿日期:2019-08-09 修回日期:2019-10-08 发布日期:2019-11-07
  • 通讯作者: 姚明, 熊航行, 刘生鹏;;
  • 基金资助:

Synthesis of Resveratrol, Piceatannol and Pinosylvin

Zhang Jingjinga,b, Yao Mingb, Li Lia,b, Sang Dayongb, Xiong Hangxinga,b, Liu Shengpenga   

  1. a School of Chemical Engineering and Pharmacy, Wuhan Institute of Technology, Wuhan 430205;
    b College of Chemical Engineering and Pharmacy, Jingchu University of Technology, Jingmen 448000
  • Received:2019-08-09 Revised:2019-10-08 Published:2019-11-07
  • Supported by:
    Project supported by the Science Technology Foundation for Creative Research Group of Hubei Department of Education (No. T201719).

A convenient method for the practical synthesis of resveratrol, piceatannol and pinosylvin is described. Resveratrol, pinosylvin and piceatannol can be achieved through a simultaneous demethylation and isomerization process from stilbenes with the aid of aluminum and iodine. The overall yields of the reaction were 68%, 78% and 56% (based on aromatic aldehyde). The solvent of the reaction can be reused after filtered. At the same time, quantum chemical calculations and control experiments show that iodine radical may be the key factor leading to cis-trans isomerization of double bond in the process of demethylation.

Key words: resveratrol, stilbene, demethylation, Wittig reaction, cis-trans isomerisation