Hydrogen Peroxide → 6-(4-Propylphenyl)-3,4,5-trifluoro-2-naphthol

Participants

Reaction Conditions

Reaction Steps

A 1.58 M butyllithium/hexane solution (16.4 ml) was added dropwise to a tetrahydrofuran (25 ml) solution of 2-(4-propylphenyl)-1,7,8-trifluoronaphthalene (6.5 g) at −65° C., and the reaction solution was stirred for 1 hour. A tetrahydrofuran (25 ml) solution of methyl iodide (3.7 g) was added dropwise to the reaction solution for 30 minutes, and then the reaction temperature was increased to 0° C. Acetic acid (1.85 ml) and 30% hydrogen peroxide (3 ml) were added to the reaction solution, followed by stirring for a while. Water was added to the reaction solution. The organic layer was removed, and the aqueous layer was extracted with ethyl acetate. The organic layers were combined, washed with water and brine, and concentrated. Then, 6-(4-propylphenyl)-3,4,5-trifluoro-2-naphthol was obtained.

Provenance & Evidence