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Transformation of 5-methoxy-1-tetralone into 8-methoxy-1-tetralone

Abstract:

The transformation of 1-hydroxy-5-methoxtetralin into 4-hydroxy-8-methoxy- 1-tetralone was accomplished in three steps (benzoylation, oxidation and alkaline hydrolysis). Treatment of the corresponding ketotosylate with sodium iodide and zinc dust in dimethoxyethane yielded the 8-methoxy-1-tetralone in 22% yield. The ketotosylate also underwent detosylation with sodium cyanoborohydride but afforded tetraol in 45% yield which on oxidation was converted into the required tetralone in 87% yield.