Dibenzoxanthene Derivatives and Related Products from β-Naphthol and Aldehydes or Acetals

Article abstract of DOI:10.1021/jo00344a014

We have investigated several reactions of β-naphthol with aldehydes or aldehyde equivalents.Many of these reactions give novel structures.For example, reaction with paraldehyde does not yield the dinaphthyl acetal as previously reported but instead a compound which we show by spectroscopic methods to be 2-methyl-4-(2-hydroxy-1-naphthyl)benzochroman.Further, reaction with methyl dimethoxyacetate gives a furanone derivative and with malondialdehyde yields a dinaphthodioxabicyclo<3.3.1> derivative.The unusual reactions limit the utility of this reaction sequence for the preparation of xanthene derivatives.