Cyclization of 5-hexynoic acid to 3-alkoxy-2-cyclohexenones

Anne T. Hylden; Eric J. Uzelac; Zeljko Ostojic; Ting-Ting Wu; Keely L. Sacry; Krista L. Sacry; Lin Xi; T. Nicholas Jones

doi:10.3762/bjoc.7.155

Beilstein Journal of Organic Chemistry (Sep 2011)

Cyclization of 5-hexynoic acid to 3-alkoxy-2-cyclohexenones

Anne T. Hylden,
Eric J. Uzelac,
Zeljko Ostojic,
Ting-Ting Wu,
Keely L. Sacry,
Krista L. Sacry,
Lin Xi,
T. Nicholas Jones

Affiliations

Anne T. Hylden: Department of Chemistry, College of St. Benedict, St. John’s University, St. Joseph, MN 56374, USA
Eric J. Uzelac: Department of Chemistry, College of St. Benedict, St. John’s University, St. Joseph, MN 56374, USA
Zeljko Ostojic: Department of Chemistry, College of St. Benedict, St. John’s University, St. Joseph, MN 56374, USA
Ting-Ting Wu: Department of Chemistry, College of St. Benedict, St. John’s University, St. Joseph, MN 56374, USA
Keely L. Sacry: Department of Chemistry, College of St. Benedict, St. John’s University, St. Joseph, MN 56374, USA
Krista L. Sacry: Department of Chemistry, College of St. Benedict, St. John’s University, St. Joseph, MN 56374, USA
Lin Xi: Department of Chemistry, College of St. Benedict, St. John’s University, St. Joseph, MN 56374, USA
T. Nicholas Jones: Department of Chemistry, College of St. Benedict, St. John’s University, St. Joseph, MN 56374, USA

DOI: https://doi.org/10.3762/bjoc.7.155
Journal volume & issue: Vol. 7, no. 1
pp. 1323 – 1326

Abstract

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The one-pot cyclization of 5-hexynoic acid to produce 3-alkoxy-2-cyclohexenones proceeds in good yields (58–90%). 3-Hexynoic acid was converted to its acyl chloride with the aid of oxalyl chloride and was cyclized to 3-chloro-2-cyclohexenone upon addition of indium(III) chloride. Subsequent addition of alcohol nucleophiles led to the desired 3-alkoxy-2-cyclohexenones.

Published in Beilstein Journal of Organic Chemistry

ISSN: 1860-5397 (Online)
Publisher: Beilstein-Institut
Country of publisher: Germany
LCC subjects: Science: Chemistry: Organic chemistry
Website: http://www.beilstein-journals.org/bjoc

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