Water → 4-(Trifluoroacetyl)toluene

HRID 975214

Reaktionsgleichung

Reaktionsgleichung von HRID 975214
[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]

Komponenten

6

Edukt 3

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

Produkt 1

HCID 1362374-(Trifluoroacetyl)toluene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 94433Tetrabutylammonium hydrogen sulfateKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-6f6296582a0f45878d52b4124c195d24
Quelldatensatz
uspto-grants-1997_03
Patentnummer
US05608062

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