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ERIC Number: EJ1159472
Record Type: Journal
Publication Date: 2017-Oct
Pages: 4
Abstractor: As Provided
ISSN: ISSN-0021-9584
Two Approaches to the Synthesis of Dimethyl Fumarate That Demonstrate Fundamental Principles of Organic Chemistry
Love, Brian E.; Bennett, Lisa J.
Journal of Chemical Education, v94 n10 p1543-1546 Oct 2017
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.
Division of Chemical Education, Inc and ACS Publications Division of the American Chemical Society. 1155 Sixteenth Street NW, Washington, DC 20036. Tel: 800-227-5558; Tel: 202-872-4600; e-mail:; Web site:
Publication Type: Journal Articles; Reports - Descriptive
Education Level: Higher Education
Audience: N/A
Language: English
Sponsor: N/A
Authoring Institution: N/A
Grant or Contract Numbers: N/A