Selective methoxy ether cleavage of 2,6-dimethoxyphenol followed by a selective acylation

A Friedel–Crafts reaction of 2,6-dimethoxyphenol in the presence of aluminum chloride and propanoyl or butanoyl chloride, respectively, lead, at elevated temperatures, to a selective cleavage of one of the methoxy groups followed by a selective acylation of the meta position with respect to the phenolic hydroxyl group. Under the same reaction conditions 2-methoxyphenol does not get demethylated; a mechanism to account for these findings is proposed. This reaction gives access to a variety of ortho-acylated catechols. Substituted catechols are widely used in supramolecular chemistry and are precursors of pesticides, flavors, and fragrances. Additionally, catechol moieties are found in various natural products.