One‐Pot Cleavage of Aryl Alkyl Ethers by Aluminum and Iodine in Acetonitrile

Abstract

AbstractCleavage of aryl alkyl ethers was conducted in a one‐pot one‐stage manner by mixing the ethers, aluminum and iodine in acetonitrile without the in situ preparation of aluminum triiodide in advance. For ethers bearing acid‐labile functional groups such as allyl, alkenyl and carbonyl, an acid scavenger (calcium oxide, 1,3‐diisopropylcarbodiimide or dimethyl sulfoxide) was used to prevent side‐reactions. This one‐pot protocol is efficient and convenient for the removal of methyl, ethyl, isopropyl and tert‐butyl groups from typical aryl alkyl ethers, catechol monomethyl and dimethyl ethers, and is compatible with a variety of functional groups including alkenyl, alkyl, allyl, amido, cyano, formyl, halogen, keto and nitro group. Methyl 2‐anisate and eugenol acetate were exhaustively deprotected by the method that afforded salicylic acid and hydroxychavicol, respectively.