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ERIC Number: EJ832499
Record Type: Journal
Publication Date: 2009-Apr
Pages: 2
Abstractor: As Provided
Reference Count: 23
ISSN: ISSN-0021-9584
Preparation of Oil of Wintergreen from Commercial Aspirin Tablets: A Microscale Experiment Highlighting Acyl Substitutions
Hartel, Aaron M.; Hanna, James M., Jr.
Journal of Chemical Education, v86 n4 p475-476 Apr 2009
A single-pot procedure for the preparation of methyl salicylate (oil of wintergreen) from commercial aspirin tablets has been developed. The synthesis proceeds via a tandem transesterification-Fischer esterification using acidic methanol and can be carried out using either conventional or microwave heating. The experiment helps demonstrate acyl substitution chemistry while generating student interest in chemistry. The experiment can be performed in approximately three hours, and the product can be used to demonstrate acquisition and interpretation of [superscript 1]H and [superscript 13]C NMR spectroscopy. (Contains 1 scheme.)
Division of Chemical Education of the American Chemical Society. Subscription Department, P.O. Box 1267, Bellmawr, NJ 08099-1267. Tel: 800-691-9846; Tel: 856-931-5825; Fax: 856-931-4115; e-mail:; Web site:
Publication Type: Journal Articles; Reports - Descriptive
Education Level: Higher Education
Audience: Teachers
Language: English
Sponsor: N/A
Authoring Institution: N/A