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Synthesis of 11 cis , 15 cis ‐ and 10 cis , 15 cis ‐Octadecadienoic acid, the probable precursors of 4 cis ‐heptenal in autoxidized butterfat
Author(s) -
Pabon H. J. J.,
Van Dorp D. A.
Publication year - 1969
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/bf02544813
Subject(s) - saponification , chemistry , stereospecificity , liquid ammonia , ammonia , cis–trans isomerism , butterfat , medicinal chemistry , organic chemistry , stereochemistry , milk fat , catalysis , linseed oil
Abstract 11 cis ,15 cis ‐ and 10 cis ,15 cis ‐Octadecadienoic acid are considered to be precursors of 4 cis ‐heptenal occurring in autoxidized butterfat. The synthesis of these acids was carried out as follows. In liquid ammonia, 1‐sodio‐1,5‐octadiyne was coupled with 1‐chloro‐9‐iodononane and 1‐sodio‐1,6‐nonadiyne with 1‐chloro‐8‐iodooctane. The 1‐chloro‐10,14‐and ‐9,14‐heptadecadiynes thus obtained were converted into 11,15‐ and 10,15‐octadecadiynoic acid. Stereospecific partial hydrogenation of the 11,15‐diynoic acid, or of the methyl 10,15‐diynoate, and subsequent saponification, yielded the acids desired.