Water → 4-(Trifluoroacetyl)toluene

HRID 975214

Reaction equation

HRID 975214 reaction equation
[F:1][C:2]([F:13])([F:12])[CH:3]([C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[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:12])([F:13])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=1)=[O:4]

Participants

6

Reactant 3

HCID 962WaterHCID 3472044-Methyl-alpha-(trifluoromethyl)benzenemethanolHCID 23665760Sodium Hypochlorite

Product 1

HCID 1362374-(Trifluoroacetyl)toluene

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

2.88 g (0.015 mol) of 2,2,2-trifluoro-1-(4-methylphenyl)ethanol and 0.26 g (0.0007 mol) of tetrabutylammonium hydrogen sulfate are dissolved in 125 ml of methylene chloride at room temperature. 9.3 ml (0.018 mol) of an approximately 12% strength sodium hypochlorite solution are metered in within 10 minutes with vigorous stirring and the mixture is stirred for a further 4 hours at room temperature. The reaction mixture is added to 100 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 (0.4 mbar, 60°-70° C. bath temperature), 0.84 g (30% of theory) of 4-trifluoroacetyltoluene are obtained. nD20 : 1.4675.

Workup

  1. customare metered in within 10 minutes
  2. stirringthe mixture is stirred for a further 4 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 (0.4 mbar, 60°-70° C. bath temperature), 0.84 g (30% of theory) of 4-trifluoroacetyltoluene
  9. customare obtained

Sources & evidence

ORD record
ord-6f6296582a0f45878d52b4124c195d24
Source dataset
uspto-grants-1997_03
Patent number
US05608062

Linked notes

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