One-pot Synthesis of 1,3-Dinitroalkanes under Heterogeneous Catalysis

Reaction of aldehydes with an excess of nitromethane in the presence of basic alumina as solid catalyst allows the one pot preparation of 1,3-dinitroalkanes. The synthesis proceeds through the nitroaldol reaction of nitromethane, which acts both as nucleofile and as solvent, to the aldehydes with the formation of beta-nitroalkanols as intermediates that convert to nitroalkenes. Further nucleophilic behavior of the nitromethane produces the in situ conjugate addition of its carbanion to the formed nitroalkanes giving the one-pot synthesis of the title compounds. The catalyst shows general applicability with aliphatic, aromatic and heteroaromatic aldehydes.