4-Hydroxybenzyl Alcohol → {4-[(3,4-Dinitrophenyl)oxy]phenyl}methanol

HRID 547609

Reaktionsgleichung

Reaktionsgleichung von HRID 547609
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1.[OH:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[N+:11]([C:4]1[CH:3]=[C:2]([O:22][C:19]2[CH:20]=[CH:21][C:16]([CH2:15][OH:14])=[CH:17][CH:18]=2)[CH:7]=[CH:6][C:5]=1[N+:8]([O-:10])=[O:9])([O-:13])=[O:12]

Komponenten

6

Edukt 4

HCID 1254-Hydroxybenzyl AlcoholHCID 10796Cesium carbonateHCID 11430Potassium CarbonateHCID 2986753,4-Dinitrofluorobenzene

Produkt 1

HCID 57585910{4-[(3,4-Dinitrophenyl)oxy]phenyl}methanolAusbeute 45,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

4-fluoro-1,2-dinitrobenzene (20.0 g, 107.5 mmol), 4-(hydroxymethyl)phenol (14.7 g, 118.2 mmol) and potassium carbonate (17.8 g, 129.0 mmol) were stirred in 250 ml of dimethylformamide at room temperature for approximately 17 hours. The reaction was heated at 35 degree Centigrade for 1.5 hours. Cesium carbonate (2 g, 6.14 mmol) was added and the reaction was heated at 45 deg. C. for approximately 22 hours. The solids were filtered away and washed with ethyl acetate. The filtrate was diluted with water and extracted 4 times with ethyl acetate. The ethyl acetate layers were washed with a water/brine mixture 5 times. The aqueous wash layers were back extracted with ethyl acetate twice. The organic layers were combined, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (0 to 100% ethyl acetate in hexane) to give 14.1 g of {4-[(3,4-dinitrophenyl)oxy]phenyl}methanol.

Aufarbeitung

  1. temperatureThe reaction was heated at 35 degree Centigrade for 1.5 hours
  2. temperaturethe reaction was heated at 45 deg. C
  3. filtrationThe solids were filtered away
  4. washwashed with ethyl acetate
  5. additionThe filtrate was diluted with water
  6. extractionextracted 4 times with ethyl acetate
  7. washThe ethyl acetate layers were washed with a water/brine mixture 5 times
  8. extractionThe aqueous wash layers were back extracted with ethyl acetate twice
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by silica gel column chromatography (0 to 100% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-1e841c2472d34406894f9a6e49077704
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07939528B2

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