Bismuth trichloride–mediated cleavage of phenolic methoxymethyl ethers

Oghale Obaro-BestDepartment of Chemistry, State University of New York at Plattsburgh, Plattsburgh, New York, USA

Jack ReedDepartment of Chemistry, State University of New York at Plattsburgh, Plattsburgh, New York, USA

Alya A. F. B. NorfadilahDepartment of Chemistry, State University of New York at Plattsburgh, Plattsburgh, New York, USA

Ryan MonahanDepartment of Chemistry, State University of New York at Plattsburgh, Plattsburgh, New York, USA

Rajesh SunaseeDepartment of Chemistry, State University of New York at Plattsburgh, Plattsburgh, New York, USACorrespondence[email protected]

ABSTRACT

A simple and efficient method for removal of phenolic methoxymethyl ethers in the presence of 30 mol% of bismuth trichloride in acetonitrile/water is described. Notable features of the cleavage protocol entail use of an ecofriendly bismuth reagent, ease of handling, low cost, operational simplicity, and good functional group compatibility. A number of structurally varied phenolic methoxymethyl ethers were cleaved in good to excellent yields.

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Acknowledgments

We thank J. Jones for NMR measurements and S. Blair, B. Rosenthals, M. McNaught, and N. Danyashah for assistance for preparing phenolic MOM ethers 2a, 4a, 8a, and 16a respectively.

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Bismuth trichloride–mediated cleavage of phenolic methoxymethyl ethers

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Bismuth trichloride–mediated cleavage of phenolic methoxymethyl ethers

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GRAPHICAL ABSTRACT

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