Water → HCID 13880754, compound

HRID 975223Notes

Reaction equation

HRID 975223 reaction equation
[F:1][C:2]([F:17])([F:16])[CH:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]([F:15])([F:14])[F:13])=[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:16])([F:17])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]([F:13])([F:14])[F:15])=[CH:7][CH:6]=1)=[O:4]

Participants

6

Reactant 3

HCID 962WaterHCID 19971592HCID 19971592, compoundHCID 23665760Sodium Hypochlorite

Product 1

HCID 13880754HCID 13880754, compound

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

24.0 g (0.09 mol) of 2,2,2-trifluoro-1-(4-trifluoromethoxyphenyl)ethanol and 1.57 g (0.0046 mol) of tetrabutylammonium hydrogen sulfate are dissolved in 250 ml of methylene chloride at room temperature. 100 ml (0.12 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 during which the temperature rises to 40° C. 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 in a kugelrohr (14 torr, bath temperature 100°-115° C.), 17.19 g (74% of theory) of 4-trifluoroacetyltrifluoromethoxybenzene are obtained. nD20 : 1.4188.

Workup

  1. customare metered in within 20 minutes
  2. stirringthe mixture is stirred for a further 5 hours during which the temperature
  3. customrises to 40° C
  4. customthe phases are separated
  5. extractionthe aqueous phase is extracted several times with methylene chloride
  6. washthe combined organic phases are washed with saturated aqueous sodium chloride solution
  7. dry with materialAfter drying the organic phase with sodium sulfate
  8. distillationthe volatiles are distilled off
  9. distillationdistillation of the crude product in a kugelrohr (14 torr, bath temperature 100°-115° C.), 17.19 g (74% of theory) of 4-trifluoroacetyltrifluoromethoxybenzene
  10. customare obtained

Sources & evidence

ORD record
ord-cd4e4f7c8b5644c5a1af503b3b873ff0
Source dataset
uspto-grants-1997_03
Patent number
US05608062

Reaction notes

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