Acetic Acid → 4-Trifluoromethanesulfonylphenol

HRID 39009Notes

Reaction equation

HRID 39009 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

5

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 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).

Workup

  1. extractionthe solution was extracted with EtOAc
  2. dry with materialThe combined organic phases were dried (Na2SO4)
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-f573fd66a98841c083f92e31280dc410
Source dataset
uspto-grants-2013_09
Patent number
US08524766B2

Reaction notes

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