Water → 2,2,2-Trifluoro-4'-(trifluoromethyl)acetophenone

HRID 975219Notes

Reaction equation

HRID 975219 reaction equation
[F:1][C:2]([F:16])([F:15])[CH:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[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:15])([F:16])[C:3]([C:5]1[CH:6]=[CH:7][C:8]([C:11]([F:12])([F:13])[F:14])=[CH:9][CH:10]=1)=[O:4]

Participants

6

Reactant 3

HCID 962WaterHCID 113908862,2,2-trifluoro-1-[4-(trifluoromethyl)phenyl]ethan-1-olHCID 23665760Sodium Hypochlorite

Product 1

HCID 1446832,2,2-Trifluoro-4'-(trifluoromethyl)acetophenone

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

25.4 g (0.1 mol) of 2,2,2-trifluoro-1-(4-trifluoromethylphenyl)ethanol and 1.76 g (0.005 mol) of tetrabutylammonium hydrogen sulfate are dissolved in 350 ml of methylene chloride at room temperature. 108 ml (0.125 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 5 hours at room temperature. The reaction mixture is added to 400 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 (18 torr, 60°-61° C.), 16.74 g (66.5% of theory) of 4-trifluoroacetyltrifluoromethylbenzene are obtained, which, according to GC, is 96.7% pure. nD20 : 1.4146.

Workup

  1. customare metered in within 20 minutes
  2. stirringthe mixture is stirred for a further 5 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 (18 torr, 60°-61° C.), 16.74 g (66.5% of theory) of 4-trifluoroacetyltrifluoromethylbenzene
  9. customare obtained

Sources & evidence

ORD record
ord-07b2f522c64344e5bd53960a9c2d68b8
Source dataset
uspto-grants-1997_03
Patent number
US05608062

Reaction notes

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