Water → 4-(4-Nitro-3-trifluoromethyl-phenoxy)-cyclohexanol

HRID 1890385Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1890385
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([C:11]([F:14])([F:13])[F:12])[CH:3]=1.[C@H:15]1([OH:22])[CH2:20][CH2:19][C@H:18]([OH:21])[CH2:17][CH2:16]1.[H-].[Na+].O>CS(C)=O>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([O:21][CH:18]2[CH2:19][CH2:20][CH:15]([OH:22])[CH2:16][CH2:17]2)=[CH:3][C:4]=1[C:11]([F:14])([F:13])[F:12])([O-:10])=[O:9]

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 2230945-Fluoro-2-nitrobenzotrifluorideHCID 178521615HCID 178521615, Verbindung

Produkt 1

HCID 672831954-(4-Nitro-3-trifluoromethyl-phenoxy)-cyclohexanolAusbeute 36 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

4-Fluoro-1-nitro-2-trifluoromethyl-benz ene (11.5 mmol), trans-cyclohexane-1,4-diol (17.2 mmol), and sodium hydride (60% in oil, 11.5 mmol) are suspended in dry dimethylsulfoxide (20 mL) and the resulting mixture is reacted under stirring for 3 hours at 50° C. The reaction is allowed to reach room temperature and is then further reacted at this temperature overnight. The reaction is treated with water (20 mL), the precipitate formed is removed by filtration and the filtrate is extracted with dichloromethane (50 mL). The organic phase is washed with aqueous saturated ammonium chloride (10 mL), dried over magnesium sulfate, filtered and the filtrate is concentrated under reduced pressure. The precipitate is triturated with diethylether (20 mL), filtered and the filtrate concentrated under reduced pressure. Both fractions of crude product are combined, dissolved in dichloromethane and filtered trough a short pad of silica gel to afford the desired product (36% yield).

Aufarbeitung

  1. customthe resulting mixture is reacted
  2. customto reach room temperature
  3. customis then further reacted at this temperature overnight
  4. customthe precipitate formed
  5. customis removed by filtration
  6. extractionthe filtrate is extracted with dichloromethane (50 mL)
  7. washThe organic phase is washed with aqueous saturated ammonium chloride (10 mL)
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationthe filtrate is concentrated under reduced pressure
  11. customThe precipitate is triturated with diethylether (20 mL)
  12. filtrationfiltered
  13. concentrationthe filtrate concentrated under reduced pressure
  14. dissolutiondissolved in dichloromethane
  15. filtrationfiltered trough a short pad of silica gel

Quellen und Nachweise

ORD-Eintrag
ord-34b6dfd2ddc54a1f9f5af7d4fb3d1874
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08507474B2

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