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A New Route to 4-Hydroxytetralones and 1-Naphthols
Broom, Nigel J. P.,Sammes, Peter G.
, p. 465 - 470 (2007/10/02)
The lithium salts, derived from position 3 of phthalides by treatment with hindered bases, participate in Michael addition reactions with a variety of conjugated olefins.For singly activated olefins the conjugate anion reacts intramolecularly with the lactone group to produce 4-hydroxytetralones in moderate to good yield.Dehydration of these hydroxytetralones, by brief treatment with acid, produces the corresponding α-naphthol.Substituted phthalides react similarly making the method a general one for the production of substituted α-naphthols.
