Synthesis of the Commercial Fragrance Compound Ethyl 6-Acetoxyhexanoate: A Multistep Ester Experiment for the Second-Year Organic Laboratory

Abstract

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.

How to Design Experiential Learning Resources for Independent Learning

“…Several chemistry and chemical engineering laboratory experiments typically use contexts that are familiar to students as the foundation. Examples of this approach include food and beverages, ,, fragrances , and even music to introduce relevant concepts such as the impact of various chemical functional groups or analytical techniques such as chromatography or spectroscopy.…”

A Visual Organic Chemistry Reaction: The Synthesis of 4-Amino-3-nitrobenzoic Acid Methyl Ester via Fischer Esterification

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Synthesis of substituted N-phenylmaleimides and use in a Diels–Alder reaction: a green multi-step synthesis for an undergraduate organic chemistry laboratory

“…The commitment of faculty to incorporating synthesis into the curriculum is evident in a large number of multi-step syntheses in Mayo's classic laboratory textbook (5) and the multitude of synthesis experiments found in the literature. These experiments provide a variety of approaches to teaching synthesis in the sophomore organic chemistry curriculum with most of them focusing on the synthesis of a biologically (6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17) or commercially (18)(19)(20)(21)(22)(23)(24) relevant target while some are designed for pedagogical (25)(26)(27)(28)(29)(30)(31)(32)(33)(34)(35)(36)(37) reasons. The complexity of the syntheses differ greatly and range from two (6, 7, 11-13, 16, 18, 20, 22, 27, 31, 36), three (8, 10, 14, 15, 17, 21, 23, 25, 28-30, 34, 37), four (9,26,33,38), five (19,32), six (24,39), and eight (40) step processes.…”