Hydrogen Peroxide → 2-Naphthol

Participants

Reaction Steps

Using a 1:1 molar mixture of fluorosulfuric acid and antimony pentafluoride diluted with sulfuryl chloride fluoride, a solvent of low nucleophilicity, the reaction of naphthalene with hydrogen peroxide (90% solution) at temperatures between -78% and -70° C., gave 54.2% of β-naphthol with 4.4% of α-naphthol. About 6% of dihydroxynaphthalenes were also formed with only traces of polymeric material and 22% naphthalene was recovered. The yield of β-naphthol is 69% with an isomeric purity of 92.5%. Similar results showing high regioselectivity in the formation of β-naphthol were also obtained in other superacidic systems, such as in hydrogen fluoride-antimony pentafluoride, hydrogen fluoride-tantalum pentafluoride, trifluoromethanesulfonic acid-antimony pentafluoride, and the like.

Provenance & Evidence