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. (C) 2011 Elsevier Ltd. All rights reserved.
Link to Published Version
Adogla, E. A., Janser, R. F. J., Fairbanks, S. S., Vortolomei, C. M., Meka, R. K., & Janser, I. (2012). Selective methoxy ether cleavage of 2,6-dimethoxyphenol followed by a selective acylation. Tetrahedron Letters, 53(1), 11–14. doi:10.1016/j.tetlet.2011.10.140