The Practical Synthesis and Purification of cis-11-Octadecenoic Acid: A Component of Inhibition of Endotoxin Response

Volume 9, Issue 1, February 2024     |     PP. 106-112      |     PDF (232 K)    |     Pub. Date: August 9, 2019
DOI:    255 Downloads     2602 Views  

Author(s)

Yoshifumi Yuasa, Kasai Chemical Laboratory, 7-7-402 Akashicho, Hiratsuka, Kanagawa, 254-0042, Japan
Akiko Horizoe, Kasai Chemical Laboratory, 7-7-402 Akashicho, Hiratsuka, Kanagawa, 254-0042, Japan

Abstract
cis-11-Octadecenoic acid 1, which is known to be a useful chemical for the component of drugs, has been synthesized by Wittig reaction with n-heptanal and 10-methoxycarbonyldecyltriphenylphosphonium bromide using potassium t-butoxide at –50 °C to give methyl cis-11-octadecenoate 2 in 79% yield with 95% cis-selectivity, followed by hydrolysis and then recrystallizated by MeOH at –20 °C to give a high purity of 1 in 33% yield.

Keywords
cis-11-Octadecenoic acid; Asclepic acid; Wittig reaction; Potassium t-butoxide; cis-Selectivity.

Cite this paper
Yoshifumi Yuasa, Akiko Horizoe, The Practical Synthesis and Purification of cis-11-Octadecenoic Acid: A Component of Inhibition of Endotoxin Response , SCIREA Journal of Chemistry. Volume 9, Issue 1, February 2024 | PP. 106-112.

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