Sodium Thiosulfate → 2-Amino-4-(trifluoromethoxy)phenol

HRID 897910

Reaktionsgleichung

Reaktionsgleichung von HRID 897910
[N+:1]([C:4]1[CH:9]=[C:8]([O:10][C:11]([F:14])([F:13])[F:12])[CH:7]=[CH:6][C:5]=1[OH:15])([O-])=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(O)C.O>[NH2:1][C:4]1[CH:9]=[C:8]([O:10][C:11]([F:12])([F:13])[F:14])[CH:7]=[CH:6][C:5]=1[OH:15]

Komponenten

5

Edukt 2

HCID 24477Sodium ThiosulfateHCID 27757752-Nitro-4-(trifluoromethoxy)phenol

Produkt 1

HCID 27377292-Amino-4-(trifluoromethoxy)phenolAusbeute 56,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a mixture of 2-nitro-4-(trifluoromethoxy)phenol (2 g, 0.0089 mol) in ethanol (50 mL) and water (25 mL) was added sodium thiosulfate (6.2 g, 0.0356 mol) at room temperature. The heterogeneous mixture was stirred at 80° C. under an atmosphere of nitrogen for 1 hour. The reaction mixture was cooled to room temperature, and ethanol was removed under reduced pressure. The aqueous layer was extracted with ethyl acetate (3×70 mL), and the organic layer was washed with brine and dried under sodium sulfate. The solvent was removed under reduced pressure to give yellow solid of 2-amino-4-(trifluoromethoxy)phenol (0.9 g, 0.005 mol). TLC (methanol/dichloromethane=5:95) Rf 0.29 MS: MH+: 194.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customethanol was removed under reduced pressure
  3. extractionThe aqueous layer was extracted with ethyl acetate (3×70 mL)
  4. washthe organic layer was washed with brine
  5. customdried under sodium sulfate
  6. customThe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c729e579dfcc42dd94c6bd422027e908
Quelldatensatz
uspto-grants-2005_07
Patentnummer
US06921763B2

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