Synthesis of 1-alkoxy-4-nitronaphthalenes in a novel nitration of naphthalene

Article abstract of DOI:10.1016/S0040-4039(97)01299-9

A new nitration of naphthalene affords as major products 1,4-disubstituted naphthalenes and as minor products 12-disubstituted naphthalenes. By use of eerie ammonium nitrate suspended on silica gel, or in homogeneous solution, nitration of naphthalene in the presence of alcohols, sodium- or tetrabutyl ammonium- nitrite and acid gives alkoxynitronaphthalenes. A preparation of 1-nitroaaphthalene is described under heterogeneous conditions.