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Synthesis of fatty 2‐oxazolines from fatty methyl 2,3‐epoxy ester
Author(s) -
Ansari M. H.,
Ahmad M.
Publication year - 1986
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/bf02540926
Subject(s) - chemistry , acrylonitrile , boron trifluoride , oxazoline , benzonitrile , acetonitrile , epoxy , catalysis , pyrolysis , organic chemistry , medicinal chemistry , polymer chemistry , copolymer , polymer
Reaction of methyl trans ‐2,3‐epoxyhexadecanoate (I) with benzonitrile in presence of boron trifluoride‐etherate (BF 3 ‐etherate) as catalyst has yielded cis ‐2‐phenyl‐4‐tridecyl‐5‐carbomethoxy‐2‐oxazoline (II), methyl 2‐hydroxy‐3‐benzamidohexadecanoate (IV) and methyl 2,3‐dihydroxyhexadecanoate (III). On the other hand, reactions of I with acetonitrile and acrylonitrile have resulted in the formation of their corresponding hydroxyamides, methyl 2‐hydroxy‐3‐acetamidohexadecanoate (VI) and methyl 2‐hydroxy‐3‐acryloamido hexadecanoate (VII), respectively, along with the product (III) only. Pyrolysis of hydroxyamides (IV), (VI) and (VII) afforded their corresponding 2‐oxazolines, cis ‐2‐phenyl‐4‐tridecyl‐5‐carboxy‐2‐oxazoline (V), cis ‐2‐methyl‐4‐tridecyl‐5‐carboxy‐2‐oxazoline (VIII) and cis ‐2‐vinyl‐4‐tridecyl‐5‐carboxy‐2‐oxazoline (IX), respectively, in good yields. The products have been characterized with the help of spectral and microanalyses.