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Saturated keto esters from lesquerolic, dimorphecolic, and densipolic acids
Author(s) -
Freedman Bernard,
Binder R. G.,
Applewhite T. H.
Publication year - 1966
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/bf02682415
Subject(s) - dehydrogenation , chemistry , reactivity (psychology) , raney nickel , catalysis , organic chemistry , medicinal chemistry , nickel , copper , medicine , alternative medicine , pathology
Summary The naturally occurring, unsaturated, hydroxy fatty esters, methyl lesquerolate (methyl 14‐hydroxy‐ cis ‐11‐eicosenoate), methyl dimorphecolate (methyl 9‐hydroxy‐ trans, trans ‐10,12‐octadecadienoate), and methyl densipolate (methyl 12‐hydroxy‐ cis , cis ‐9,15‐octadecadienoate) have been converted to the corresponding saturated keto esters by tow routes. The unsaturated esters were subjected to a hydrogenation‐dehydrogenation reaction in the presence of Raney nickel or their saturated derivatives were dehydrogenated by copper chromite catalysis. Yields of the keto esters are 65舑82% in the nickel‐catalyzed reactions, and 71舑94% by copper chromite‐catalyzed dehydrogenation. In the hydrogenation‐dehydrogenation system the order of reactivity is: methyl lesquerolate>methyl dimorphecolate>methyl densipolate. Relationships between structure and reactivity of these compounds, methyl 12‐hydroxystearate, and methyl ricinoleate are discussed.