Resorcinol → 2-Methylresorcinol

The synthetic routes to an alkylresorcinol that is partially alkylated at a position other than the 4th position on the aromatic ring are multistep and give low overall yields. For example, a 50% yield of a 2-methylresorcinol is obtained by hydrogenation of resorcinol and methylation of the resulting dihydroresorcinol to 2-methylcyclohexane-1,3-dione which on treatment with bromine is converted into 4,6-dibromo-2-methylresorcinol and finally hydrogenolysis of the dibromo derivative to produce the 2-methylresorcinol. Another example is that 5-methylresorcinol can be prepared by a five-step synthesis starting with p-toluidine or a four-step synthesis starting from ethyl crotonate. The five-step synthesis involves acetylation, two-step nitration, reductive hydrogenation, and hydrolysis.