ERIC Number: EJ1154140
Record Type: Journal
Publication Date: 2017-Sep
Abstractor: As Provided
Synthesis of the Commercial Fragrance Compound Ethyl 6-Acetoxyhexanoate: A Multistep Ester Experiment for the Second-Year Organic Laboratory
McCullagh, James V.; Hirakis, Sophia P.
Journal of Chemical Education, v94 n9 p1347-1351 Sep 2017
This synthesis of ethyl 6-acetoxyhexanoate (Berryflor) is designed as an experiment for use in a second-year organic chemistry course focusing on the synthesis and reaction of esters. The compound is described as having a raspberry-like odor with jasmine and anise aspects. A two-step procedure for its synthesis beginning with inexpensive e-caprolactone is described. The first step involves an acid-catalyzed transesterification of the lactone to form ethyl 6-hydroxyhexanoate. Ethyl 6-hydroxyhexanoate is converted to the desired compound via acetylation under mildly basic conditions to give ethyl 6-acetoxyhexanoate in good yield. The product is characterized using [superscript 1]H NMR spectroscopy, IR spectroscopy, gas chromatography, thin layer chromatography, and by comparison to commercial samples.
Descriptors: College Science, Undergraduate Study, Organic Chemistry, Science Experiments, Laboratory Experiments, Science Laboratories, Spectroscopy, Measurement Equipment, Hands on Science, Olfactory Perception
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Publication Type: Journal Articles; Reports - Descriptive
Education Level: Higher Education
Authoring Institution: N/A
Grant or Contract Numbers: N/A