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Nitration of methyl oleate with acetyl nitrate: A synthesis of methyl aminostearate
Author(s) -
Malins D. C.,
Houle C. R.
Publication year - 1963
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/bf02654737
Subject(s) - nitration , chemistry , nitro , nitrate , reagent , catalysis , organic chemistry , derivative (finance) , nitro compound , methyl oleate , nitrogen , alkyl , financial economics , economics
Abstract Acetyl nitrate, an effective reagent for the nitration of simple alkenes, provided a convenient means of introducing nitrogen into unsaturated fatty acids. This nitrating agent was found to react quantitatively under mild conditions with methyl oleate forming isomeric nitro, acetoxy‐nitro, and nitro‐nitrate derivatives. These nitro derivatives were isolated by column and thin‐layer adsorption chromatography, and their structures were elucidated by infrared spectroscopy. In addition, the isomeric nitro derivative was reduced by catalytic hydrogenation to give methyl aminostearate.