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■ Synthesis of meta-Substituted 9-Phenylxanthenes

John L. Hinds, Shirish N. Rajadhyaksha, and Joseph D. Wander

*Department of Chemsitry, The University of Georgia, Athens, Georgia 30602, U.S.A.

Abstract

Construction of the dibenzopyran ring of 9-(3-methoxyphenyl)xanthene (2) by an aluminum chloride-catalyzed, geminal dialkylation reaction between 3-methoxybenzal chloride and phenyl ether was accomplished, but in poor yield; however, a satisfactory preparation of 2 was attained by the grignard reaction of 3-methoxyphenylmagnesium iodide with xanthone, and subsequent reduction; demethylation of 2 was effected by treatment with trimethylsilyl iodide in hot quinoline.