Hydrogen Peroxide → 2-Naphthol

Participants

Reaction Steps

0.1 mol of naphthalene was dissolved at -78° C. in a solution of 50 ml of 1:1 mol/mol FSO3H--SbF5 in 100 ml of sulfuryl chloride fluoride. 0.12 mol of H2O2 (90% solution) was separately dissolved in a solution of 50 ml of 1:1 (m/m) FSO2H--SbF5 and 100 ml of sulfuryl chloride fluoride at the same temperature. The H2O2 superacid solution was carefully added with good stirring at -78° to -70° C. to the superacid solution of naphthalene and the reaction mixture subsequently was stirred for an additional 30 minutes, then quenched with ice water, worked up, and analyzed as in Example 1. 22% naphthalene was recovered unchanged. 54.2% of β-naphthol and 4.4% of naphthol were obtained, together with 6% dihydroxynaphthalenes and only traces of polymeric material.

Provenance & Evidence