Mesyl guaiacol: a versatile intermediate for the synthesis of 5-aminomethyl guaiacol and related compounds

An original synthetic pathway for the preparation of 5-substituted guaiacol derivatives is described. This method relies on the deactivation of the phenol group by converting it into the corresponding mesyl ester. Amidomethylation reactions lead to regioselective CC bond formation at the 5-position of guaiacol. Thus, 5-aminomethyl-guaiacol was obtained in four steps and 75% overall yield.