Nitration of methyl oleate with acetyl nitrate: A synthesis of methyl aminostearate

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.