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Citation: Yanji Huang, Binyang Liu, Min Yu, Min Lin, Jinmei Zhou, Lirong Lin. Improvement and Extensive Design of the Synthesis of Coumarin-3-carboxylic Acid[J]. University Chemistry, ;2023, 38(2): 214-220. doi: 10.3866/PKU.DXHX202205061 shu

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

Yanji Huang ¹ ,
Binyang Liu ¹ ,
Min Yu ¹ ,
Min Lin ² ,
Jinmei Zhou ² ,
Lirong Lin 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 Date: 18 May 2022

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 °C 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.
- Coumarin-3-carboxylic acid,
- Knoevenagel condensation reaction,
- Fluorescence,
- Energy transfer
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