Two Approaches to the Synthesis of Dimethyl Fumarate That Demonstrate Fundamental Principles of Organic Chemistry
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Brian E. Love [1] ; Lisa J. Bennett [1]
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[1] East Carolina University
East Carolina University
Township of Greenville, Estados Unidos
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- Localización: Journal of chemical education, ISSN 0021-9584, Vol. 94, Nº 10, 2017, págs. 1543-1546
- Idioma: inglés
- Texto completo no disponible (Saber más ...)
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Resumen
Two experiments are described which lead to the preparation of dimethyl fumarate, a compound currently used in the treatment of multiple sclerosis. Preparation of a compound with “real-world” applications is believed to increase student interest in the experiment. One experiment involves the isomerization of dimethyl maleate to the target compound through reversible nucleophilic addition of an amine, assisted by a Lewis acid catalyst. This experiment facilitates a discussion of the requirements for nucleophilic addition to alkenes, Lewis acid catalysis of carbonyl-based reactions, as well as stereochemical effects on compound stability and physical properties, such as melting point. As the experiment involves heating a solution at reflux, the rationale for and the equipment involved in this technique can also be discussed. The second experiment involves a classic Fischer esterification. This not only reinforces a reaction students will have studied in their lecture class but also facilitates a discussion of how reversible reactions can be driven toward product formation through an application of LeChatelier’s principle. Additionally, the product crystallizes out of the reaction mixture in a rather dramatic fashion, making the experiment visually memorable. The fact that the same compound can be made by two entirely different reactions helps illustrate the point that even simple compounds can be prepared by a variety of synthetic routes.
