title: Selective methoxy ether cleavage of 2,6-dimethoxyphenol followed by a selective acylation.
abstract: A Friedel-Crafts reaction of 2,6-dimethoxyphenol in the presence of aluminum chloride and propanoyl or butanoyl chlorid, 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 doesn't 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.
authors.affiliation: Laboratory of Organic Synthesis, Catalysis & Biochemistry (LOSCB), Department of Chemistry, New Mexico Institute of Mining and Technology, 801 Leroy Place, Socorro, NM 87801, USA.
authors.forename: Enoch A
authors.initials: EA
authors.lastname: Adogla
authors.forename: Romy F J
authors.initials: RF
authors.lastname: Janser
authors.forename: Samuel S
authors.initials: SS
authors.lastname: Fairbanks
authors.forename: Caitlyn M
authors.initials: CM
authors.lastname: Vortolomei
authors.forename: Ranjith K
authors.initials: RK
authors.lastname: Meka
authors.forename: Ingo
authors.initials: I
authors.lastname: Janser