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Application of Ionic Liquid Halide Nucleophilicity for the Cleavage of Ethers: A Green Protocol for the Regeneration of Phenols from Ethers

Shanthaveerappa K. Boovanahalli, Dong Wook Kim and Dae Yoon Chi*

*Department of Chemistry, Sogang University, 1 Shinsudong, Mapoku, Seoul 121-742, Korea, Email: dychisogang.ac.kr

S. K. Boovanahalli, D. W. Kim, D. Y. Chi, J. Org. Chem., 2004, 69, 3340-3344.

DOI: 10.1021/jo035886e (free Supporting Information)


Abstract

The ionic liquid [bmim][Br] confers high nucleophilicity on the bromide ion for the nucleophilic displacement of an alkyl group to regenerate a phenol from the corresponding aryl alkyl ether in good yield in the presence of p-toluenesulfonic acid. Dealkylation of various aryl alkyl ethers could also be achieved using stoichiometric amounts of concentrated hydrobromic acid in [bmim][BF4].

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Key Words

Ether Cleavage, Benzyl Ethers, Green Chemistry, Ionic Liquids


ID: J42-Y2004-420