Epoxidation of ethyl (Z)-9-(Z)-12-(Z)-15-octadecatrienoate with m-chloroperbenzoic acid

✍ Scribed by M. Alaiz; M.P. Maza; R. Zamora; F.J. Hidalgo; F. Millán; E. Vioque

• Book ID: 103040831
• Publisher: Elsevier Science
• Year: 1989
• Tongue: English
• Weight: 272 KB
• Volume: 49
• Category: Article
• ISSN: 0009-3084
• DOI: 10.1016/0009-3084(89)90069-8

✦ Synopsis

The expoxidation of ethyl linolenate (ethyl (Z)-9-(Z)-12-(Z)-15-octadecatrienoate) (i) with m-chloroperbenzoic acid is described. When the reaction was performed using one mole of peracid per mole of (i), the three monoepoxides of (i), namely, ethyl c/s-9,10-epoxy-(Z)-12-(Z)-15-octadecadienoate (if), ethyl c/s-12,13-epoxy-(Z)-9-(Z)-lS-octadecadienoate (ill) and ethyl c/s-15,16epoxy-(Z)-9-(Z)-12-octadecadienoate (IV) were the main products; these compounds were isolated by thin-layer chromatography. Using 3 tool peracid/mol of (I), ethyl c/s-9,10-c/s-12,13-c/s-15,16-triepoxy-octadecanoate (XIV) was obtained. The compounds were characterized by spectroscopic techniques and derivative preparation.