Acetic Acid → 4-Trifluoromethanesulfonylphenol

Reaction equation

[F:1][C:2]([F:12])([F:11])[S:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.OO.[OH-:15].[Na+].C(O)(=[O:19])C>>[F:12][C:2]([F:11])([F:1])[S:3]([C:4]1[CH:5]=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=1)(=[O:19])=[O:15]

Participants

Reactant 4

HCID 176Acetic Acid

HCID 784Hydrogen Peroxide

HCID 14798Sodium Hydroxide

HCID 38151584-(Trifluoromethylsulfanyl)phenol

Product 1

HCID 148574264-Trifluoromethanesulfonylphenol

Conditions

Temperature: 65 °C

Procedure

A mixture of 4-[(trifluoromethyl)thio]phenol (4.5 g, 23.2 mmol), Na2WO4.2H2O (0.08 g, 0.24 mmol) and hydrogen peroxide (6 ml, 59 mmol) in acetic acid (25 ml) was heated at 65° C. for overnight. Na2S2O5 (sat.) and NaOH (20%) was added (until pH 8) and the solution was extracted with EtOAc. The combined organic phases were dried (Na2SO4) and evaporated to dryness to give the crude title compound (6.0 g). MS m/z (rel. intensity, 70 eV) 226 (M+, 18), 157 (bp), 109 (14), 93 (52), 65 (53).