Synthesis of 2-Naphthols via a Trifluoroacetic Acid-Mediated Epoxy Alcohol Rearrangement

Epoxy alcohols derived from 2-benzylidene-1-indanones undergo rearrangement to 2-naphthols when exposed to trifluoroacetic acid. The reaction sequence tolerates a variety of functional groups from both the parent indanone and the benzaldehyde derivatives. No chromatographic purification is required until the final synthetic step, and the epoxy alcohol syntheses use only water and alcohols as solvents. The synthesis is operationally simple, and the 2-naphthol products can be easily derivatized into pharmaceutically relevant compounds.