Synthesis of the Commercial Fragrance Compound Ethyl 6-Acetoxyhexanoate: A Multistep Ester Experiment for the Second-Year Organic Laboratory
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James V. McCullagh [1] ; Sophia P. Hirakis [1]
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[1] Manhattan College
Manhattan College
Estados Unidos
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- Localización: Journal of chemical education, ISSN 0021-9584, Vol. 94, Nº 9, 2017, págs. 1347-1351
- Idioma: inglés
- Texto completo no disponible (Saber más ...)
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Resumen
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 ε-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 1H NMR spectroscopy, IR spectroscopy, gas chromatography, thin layer chromatography, and by comparison to commercial samples.
