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Synthesis of cis ‐12, 13‐epoxy‐ cis ‐9‐octadecenol and 12(13)‐hydroxy‐ cis ‐9‐octadecenol from vernonia oil using lithium aluminum hydride
Author(s) -
Elhilo Eisa B.,
Anderson Melissa A.,
Ayorinde Folahan O.
Publication year - 2000
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/s11746-000-0139-9
Subject(s) - chemistry , hexane , tetrahydrofuran , lithium (medication) , epoxy , yield (engineering) , hydride , reactivity (psychology) , proton nmr , organic chemistry , alcohol , solvent , materials science , medicine , alternative medicine , pathology , metallurgy , endocrinology , hydrogen
Reduction of vernonia oil methyl esters (VOME) into epoxy fatty alcohol and diols was achieved with lithium aluminum hydride (LAH), under reflux and room temperature conditions, by using hexane and tetrahydrofuran (THF) as solvents. The reactions of VOME with LAH in hexane produced cis ‐12,13‐epoxy‐ cis ‐9‐octadecenol as a major product with an isolated yield of 73.6%, whereas the reaction with LAH in THF gave isomers of 12(13)‐hydroxy‐ cis ‐9‐octadecenol as the major products with an isolated yield of 95.1%. LAH was similarly reacted with vernonia oil (VO) to give the same products in lower yields. 1 H nuclear magnetic resonance (NMR), 13 C NMR, gas chromatography‐mass spectrometry, and infrared were used to characterize these products. This study demonstrates the ability to control the reactivity of the epoxy functionality in VO or VOME with the choice of polar or nonpolar solvents, and extends the range of oleochemicals that can be derived from vernonia oil.