Polyunsaturated nitroalkanes and nitro-substituted fatty acids

Nitroalkanes 4 are readily prepared from naturally derived polyunsaturated fatty alcohols 1 via succesive conversion to the corresponding haloalkanes 2 and 3, and reaction with silver nitrite. Reaction of nitroalkanes 4a,b wi th methyl acrylate, followed by ester hydrolysis, affords nitro-substituted fatty acids 6a,b and 8a,b. Oxidation of alcohols la,b gives the correspond ing aldehydes 9a,b, which react by Henry condensation with nitromethane to give beta -hydroxynitroalkanes 10a,b.