Abstract Improved routes for syntheses of gram quantities of the isomeric 5, 6- acetoxymethoxyindoles, and milligram amounts of the 5, 6-hydroxymethoxyindoles, have been developed. They depend on regiospecific nitration of the benzyl ethers of vanillin and isovanillin as the first steps. Improved condensations of 4, 5-acetoxymethoxy-2- nitrobenzaldehydes with nitromethane gave 4, 5-acetoxymethoxy-2, β-dinitrostyrenes as ...