Chin. J. Org. Chem. ›› 2008, Vol. 28 ›› Issue (09): 1572-1577. Previous Articles     Next Articles

Original Articles

电羧化苯乙烯基苯基酮合成2,4-二苯基-4-丁酮酸

林美玉; 王 欢; 张爱健 ; 张贵荣 ; 陆嘉星*   

  1. 华东师范大学化学系 上海市绿色化学与化工过程绿色化重点实验室 上海 200062
  • 收稿日期:2007-10-13 修回日期:2008-03-20 发布日期:2008-09-20
  • 通讯作者: 陆嘉星

Electrocarboxylation of Benzalacetophenone: Synthesis of 2,4-Diphenyl-4-oxobutanoic acid

LIN, Mei-Yu; WANG, Huan; ZHANG, Ai-Jian ; ZHANG, Gui-Rong ; LU, Jia-Xing*   

  1. Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry,
    East China Normal University, Shanghai 200062
  • Received:2007-10-13 Revised:2008-03-20 Published:2008-09-20
  • Contact: LU, Jia-Xing

Electrocarboxylation of benzalacetophenone was studied in the presence of an atmospheric pressure of CO2. The only carboxylic product obtained was 2,4-diphenyl-4-oxobutanoic acid in a one-compartment electrochemical cell equipped with magnesium as the sacrificial anode, copper (Cu), nickel (Ni), titanium (Ti), graphite (C) and stainless steel as the cathode and Ag/AgI as the reference electrode under the controlled potential conditions. Influences of solvents, electrolytes, the cathode materials, electrolysis potentials, the concentrations of substrate and temperatures were studied to improve the electrolysis yield. The results show that the electrolysis conditions have an important influence on the yield. The maximal yield reached 88% when the electrolysis was carried out in MeCN-0.1 mol•L-1 TEABF4 on Mg-stainless steel under a controlled potential of -1.75 V vs. Ag/AgI until 2 F•mol-1 of charge had passed through the cell at 0 ℃. The electrochemical behavior of benzalacetophenone has been studied in MeCN. The mechanism of the electrocarboxylation process involves a one-electron reduction and a chemical reaction followed by another one-electron reduction and a chemical reaction.

Key words: CO2, 2,4-diphenyl-4-oxobutanoic acid, electrosynthesis, benzalacetophenone