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Synthesis of methyl 9,12‐epoxyoctadecanoate from castor oil
Author(s) -
Mhaskar S. Y.,
Mani V. V. S.
Publication year - 1994
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/bf02540670
Subject(s) - dichloromethane , chemistry , tetrahydrofuran , castor oil , catalysis , organic chemistry , bromine , disulfide bond , solvent , biochemistry
We report here the synthesis of methyl 9,12‐epoxyoctadecanoate (2‐[7‐methoxycarbonyl‐heptyl]‐5‐hexanyl‐tetrahydrofuran). Methyl ricinoleate (methyl 12‐hydroxy‐9‐ cis ‐octadecenoate), isolated from castor oil methyl esters was isomerized with diphenyl disulfide as radical initiator under ultraviolet radiation to give the trans isomer, methyl ricinelaidate. The latter was cyclized by slow addition of 10% bromine solution in dichloromethane to give methyl 10‐bromo‐9,12‐epoxyoctadecanoate, which on hydrogenation with Pd/C catalyst gave the title compound, methyl 9,12‐epoxyoctadecanoate.