Volume 4, Number 3 (2019)
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Home > Journals > SCIREA Journal of Chemistry > Archive > Paper Information

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

Volume 4, Issue 3, June 2019    |    PP. 106-112    |PDF (232 K)|    Pub. Date: August 9, 2019
37 Downloads     680 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. Vol. 4 , No. 3 , 2019 , pp. 106 - 112 .

References

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