A Convenient Synthesis of (4S, 6Z)- and (4S, 6E)-6- Dodecen-4-olide, Known to Significantly Contribute to Milk Flavor

International Journal of Applied Chemistry

© 2022 by SSRG - IJAC Journal

Volume 9 Issue 3

Year of Publication : 2022

Authors : Yoshifumi Yuasa, Akiko Horizoe

10.14445/23939133/IJAC-V9I3P101

How to Cite?

Yoshifumi Yuasa, Akiko Horizoe, "A Convenient Synthesis of (4S, 6Z)- and (4S, 6E)-6- Dodecen-4-olide, Known to Significantly Contribute to Milk Flavor," SSRG International Journal of Applied Chemistry, vol. 9,  no. 3, pp. 1-4, 2022. Crossref, https://doi.org/10.14445/23939133/IJAC-V9I3P101

Abstract:

A new synthesis route of (4S, 6Z)-6-dodecen-4-olide 1 and (4S, 6E)-6-dodecen-4-olide 2, which are known to flavor milk, is described. The condensation of (R)-epichlorohydrin and 1-hepytne using vinylmagnesium chloride gave (R)- clorohydrin 3. 3 was reacted with dimethyl malonate, followed by hydrolysis and decarboxylation to give the (R)-lactone 4. 4 was hydrogenated with the Lindlar catalyst to give 1 in a total 49% yield. The cis-trans-isomerization of 1 using ptoluenesulfinic acid gave 2 in 64% yield.

Keywords:

(4S, 6Z)-6-dodecen-4-olide, (4S, 6E)-6-dodecen-4-olide, (R)-epichlorohydrin, 1-heptyne, Cis-trans-isomerization.

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