Synthesis of the Commercial Fragrance Compound Ethyl 6-Acetoxyhexanoate: A Multistep Ester Experiment for the Second-Year Organic Laboratory
1
Department of Chemistry & Biochemistry, Manhattan College, Riverdale, New York 10471-4098, United States
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Publication type: Journal Article
Publication date: 2017-06-29
scimago Q2
wos Q1
SJR: 0.596
CiteScore: 4.7
Impact factor: 2.9
ISSN: 00219584, 19381328
General Chemistry
Education
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 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 1H NMR spectroscopy, IR spectroscopy, gas chromatography, thin layer chromatography, and by comparison to commercial samples.
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Mccullagh J. V., Hirakis S. P. Synthesis of the Commercial Fragrance Compound Ethyl 6-Acetoxyhexanoate: A Multistep Ester Experiment for the Second-Year Organic Laboratory // Journal of Chemical Education. 2017. Vol. 94. No. 9. pp. 1347-1351.
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Mccullagh J. V., Hirakis S. P. Synthesis of the Commercial Fragrance Compound Ethyl 6-Acetoxyhexanoate: A Multistep Ester Experiment for the Second-Year Organic Laboratory // Journal of Chemical Education. 2017. Vol. 94. No. 9. pp. 1347-1351.
Cite this
RIS
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TY - JOUR
DO - 10.1021/acs.jchemed.6b00778
UR - https://doi.org/10.1021/acs.jchemed.6b00778
TI - Synthesis of the Commercial Fragrance Compound Ethyl 6-Acetoxyhexanoate: A Multistep Ester Experiment for the Second-Year Organic Laboratory
T2 - Journal of Chemical Education
AU - Mccullagh, James V
AU - Hirakis, Sophia P
PY - 2017
DA - 2017/06/29
PB - American Chemical Society (ACS)
SP - 1347-1351
IS - 9
VL - 94
SN - 0021-9584
SN - 1938-1328
ER -
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BibTex (up to 50 authors)
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@article{2017_Mccullagh,
author = {James V Mccullagh and Sophia P Hirakis},
title = {Synthesis of the Commercial Fragrance Compound Ethyl 6-Acetoxyhexanoate: A Multistep Ester Experiment for the Second-Year Organic Laboratory},
journal = {Journal of Chemical Education},
year = {2017},
volume = {94},
publisher = {American Chemical Society (ACS)},
month = {jun},
url = {https://doi.org/10.1021/acs.jchemed.6b00778},
number = {9},
pages = {1347--1351},
doi = {10.1021/acs.jchemed.6b00778}
}
Cite this
MLA
Copy
Mccullagh, James V., and Sophia P Hirakis. “Synthesis of the Commercial Fragrance Compound Ethyl 6-Acetoxyhexanoate: A Multistep Ester Experiment for the Second-Year Organic Laboratory.” Journal of Chemical Education, vol. 94, no. 9, Jun. 2017, pp. 1347-1351. https://doi.org/10.1021/acs.jchemed.6b00778.