Improvement of the Ethyl Acetoacetate Preparation Experiment: A Green Chemistry Experiment

The preparation of ethyl acetoacetate is a distinctive, century-old classic organic chemistry laboratory project. Ethyl acetate and sodium metal (sodium ethoxide) are reacted by Claisen ester condensation to produce the sodium salt of ethyl acetoacetate and then obtain the refined product by acidifi...

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Bibliographic Details
Published in:Journal of chemical education 2023-02, Vol.100 (2), p.811-814
Main Authors: Tan, Da-Zhi, Li, Ming-Ze, Xiong, Wan-nan, Xu, Yi-Xuan, Pan, Yang, Fan, Wen-Jie, Jiang, Wen-Feng
Format: Article
Language:English
Subjects:
Acidification
Calcium chloride
Chemicals
Condensates
Condensation
Distillation
Ethanol
Ethyl acetate
Evaporation
Green chemistry
Organic chemistry
Sodium
Sodium salts
Washing
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Summary:The preparation of ethyl acetoacetate is a distinctive, century-old classic organic chemistry laboratory project. Ethyl acetate and sodium metal (sodium ethoxide) are reacted by Claisen ester condensation to produce the sodium salt of ethyl acetoacetate and then obtain the refined product by acidification as well as washing, drying, and distillation under reduced pressure. This article analyzed the reasons for the low product yield and poor purity of the traditional experimental method and found that ethanol was the key to the final product. The improved experimental method used rotary evaporation and washing with saturated calcium chloride solution to remove ethanol. The new experimental method not only retains the characteristics of the original experiment and improves the product yield, but also adds the interesting phenomenon of pointing water into “ice”, which cultivates students’ learning interest and innovation and achieves a good teaching effect.
ISSN:0021-9584
1938-1328
DOI:10.1021/acs.jchemed.2c00718