University Chemistry ›› 2023, Vol. 38 ›› Issue (2): 214-220.doi: 10.3866/PKU.DXHX202205061

• Chemistry Laboratory • Previous Articles     Next Articles

Improvement and Extensive Design of the Synthesis of Coumarin-3-carboxylic Acid

Yanji Huang1, Binyang Liu1, Min Yu1, Min Lin2, Jinmei Zhou2,*(), Lirong Lin1,*()   

  1. 1 College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, Fujian Province, China
    2 National Demonstration Center for Experimental Chemistry Education, Xiamen University, Xiamen 361005, Fujian Province, China
  • Received:2022-05-18 Accepted:2022-07-21 Published:2022-08-02
  • Contact: Jinmei Zhou, Lirong Lin E-mail:jmzhou@xmu.edu.cn;linlr@xmu.edu.cn

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Abstract:

The preparation of coumarin-3-carboxylic acid is a classical chemistry experiment. In this experiment, the reactants, salicylaldehyde and diethyl malonate, as well as the piperidine catalyst are mixed under reflux for 2 h to obtain coumarin-3-carboxylic acid after base hydrolysis and acidification. We have made the following improvements and extensive designs to the experiment: 1) By substituting diethyl malonate with Meldrum's acid, coumarin-3-carboxylic acid can be obtained by heating at 90 ℃ for 30 min in water, and 7-(diethylamino)coumarin-3-carboxylic acid can be synthesized by changing the substrate; 2) Observing the fluorescence of the solution with Eu3+, coumarin-3-carboxylic acid, and 7-(diethylamino)coumarin-3-carboxylic acid and using computational chemistry can help verify the energy transfer property. The modified experiment, which involves a number of important multidisciplinary knowledge points, has strong modularity, comprehensiveness, interest, and teaching feasibility. Moreover, it is conducive to cultivating students' innovative and comprehensive application abilities.

Key words: Coumarin-3-carboxylic acid, Knoevenagel condensation reaction, Fluorescence, Energy transfer