Water → 1-Cyclohexyl-2,2,2-trifluoro-ethanone

HRID 975220Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 975220
[F:1][C:2]([F:12])([F:11])[CH:3]([CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)[OH:4].Cl[O-].[Na+].O>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[CH:5]1([C:3]([C:2]([F:1])([F:11])[F:12])=[O:4])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1

Komponenten

6

Edukt 3

HCID 962WaterHCID 109430921-Cyclohexyl-2,2,2-trifluoroethan-1-olHCID 23665760Sodium Hypochlorite

Produkt 1

HCID 2384151-Cyclohexyl-2,2,2-trifluoro-ethanone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 94433Tetrabutylammonium hydrogen sulfateKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

10.67 g (0.059 mol) of 2,2,2-trifluoro-1-cyclohexylethanol and 0.98 g (0.003 mol) of tetrabutylammonium hydrogen sulfate are dissolved in 250 ml of methylene chloride at room temperature. 37 ml (0.069 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 4 hours during which the reaction temperature rises to 30° C. 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 (28 torr, 80°-82° C.), 4.86 g (46% of theory) of trifluoromethyl cyclohexyl ketone are obtained. nD20 : 1.4043.

Aufarbeitung

  1. customare metered in within 20 minutes
  2. stirringthe mixture is stirred for a further 4 hours during which the reaction temperature
  3. customrises to 30° 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 (28 torr, 80°-82° C.), 4.86 g (46% of theory) of trifluoromethyl cyclohexyl ketone
  10. customare obtained

Quellen und Nachweise

ORD-Eintrag
ord-6fdde7091865485f8faa9896d0827d50
Quelldatensatz
uspto-grants-1997_03
Patentnummer
US05608062

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