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Fatty acids: Part 26.1 partial synthesis of C 18 mono‐and dimethyl furanoid fatty esters
Author(s) -
Jie M. S. F. Lie Ken,
Ahmad F.
Publication year - 1983
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/bf02680355
Subject(s) - methyl iodide , chemistry , epoxy , methylene , organic chemistry , iodide , methanol , methylation , biochemistry , gene
Dimethylene interrupted dioxo derivatives of 10, 13‐epoxy‐11‐methylocadeca‐10, 12‐dienoate (from latex) and 9 (10), 12 (13)‐epoxyoctadeca‐9 (10), 11 (12)‐dienoates (from linoleate) were successfully methylated at the methylene carbons located between the two oxo groups using methyl iodide and KOH in DMSO. The resulting dimethyldioxo derivatives were cyclodehydrated to furnish methyl 10, 13‐epoxy‐11, 12‐dimethyloctadeca‐10, 12‐dienoate and a mixture of methyl 9(10), 12(13)‐epoxy‐10(11), 11(12)‐dimethyl‐octadeca‐9(10), 11(12)‐dienoate. Similarly, methylation at C‐11 of methyl 12‐oxo‐octadec‐as‐9‐enoate (from methyl ricinoleate) gave methyl 9, 12‐epoxy, 11‐methyloctadeca‐9, 11‐dienoate on cyclodehydration.