Water → 2,2,2-Trifluoroacetophenone

HRID 975218Notes

Reaction equation

HRID 975218 reaction equation
[F:1][C:2]([F:12])([F:11])[CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[OH:4].Cl[O-].[Na+].O>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[F:1][C:2]([F:11])([F:12])[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4]

Participants

6

Reactant 3

HCID 962WaterHCID 95556(S)-alpha-(Trifluoromethyl)benzyl alcoholHCID 23665760Sodium Hypochlorite

Product 1

HCID 99052,2,2-Trifluoroacetophenone

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

10.0 g (0.057 mol) of 2,2,2-trifluoro-1-phenylethanol and 0.96 g (0.0028 mol) of tetrabutylammonium hydrogen sulfate are dissolved in 250 ml of methylene chloride at room temperature. 35 ml (0.068 mol) of an approximately 12% strength sodium hypochlorite solution are metered in within 20 minutes with vigorous stirring and the mixture is stirred for a further 6 hours at room temperature. The reaction mixture is added to 200 ml of water, the phases are separated, the aqueous phase is extracted several times with methylene chloride and the combined organic phases are washed with saturated aqueous sodium chloride solution. After drying the organic phase with sodium sulfate, the volatiles are distilled off. Following distillation of the crude product in a kugelrohr (24 torr, 90°-115° C. bath temperature), 7.45 g (75% of theory) of trifluoroacetylbenzene are obtained. nD20 : 1.4658.

Workup

  1. customare metered in within 20 minutes
  2. stirringthe mixture is stirred for a further 6 hours at room temperature
  3. customthe phases are separated
  4. extractionthe aqueous phase is extracted several times with methylene chloride
  5. washthe combined organic phases are washed with saturated aqueous sodium chloride solution
  6. dry with materialAfter drying the organic phase with sodium sulfate
  7. distillationthe volatiles are distilled off
  8. distillationdistillation of the crude product in a kugelrohr (24 torr, 90°-115° C. bath temperature), 7.45 g (75% of theory) of trifluoroacetylbenzene
  9. customare obtained

Sources & evidence

ORD record
ord-1a18d78942494835add82f0922c806e9
Source dataset
uspto-grants-1997_03
Patent number
US05608062

Reaction notes

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