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ERIC Number: EJ1154140
Record Type: Journal
Publication Date: 2017-Sep
Pages: 5
Abstractor: As Provided
ISSN: ISSN-0021-9584
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.
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: Teachers
Language: English
Sponsor: N/A
Authoring Institution: N/A
Grant or Contract Numbers: N/A