4-Nitrophenol → 2-(4-Nitrophenoxy)ethanol

HRID 351900Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 351900
[CH:1]1[C:6]([N+:7]([O-:9])=[O:8])=[CH:5][CH:4]=[C:3]([OH:10])[CH:2]=1.Cl[CH2:12][CH2:13][O:14][Si](C)(C)C.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C)C=O.C(OCC)(=O)C.C(=O)([O-])[O-].[Cs+].[Cs+]>[N+:7]([C:6]1[CH:5]=[CH:4][C:3]([O:10][CH2:12][CH2:13][OH:14])=[CH:2][CH:1]=1)([O-:9])=[O:8]

Komponenten

8

Edukt 4

HCID 9804-NitrophenolHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 2628232-Chloroethoxytrimethylsilane

Produkt 1

HCID 853812-(4-Nitrophenoxy)ethanolAusbeute 68,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 10796Cesium carbonateKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

A mixture of p-nitrophenol (1.39 g, 10 mmol), 2-chloroethoxytrimethylsilane (3.2 ml, 20 mmol), potassium carbonate (4.15 g, 30 mmol), cesium carbonate (163 mg, 0.5 mmol), and sodium iodide (149 mg, 1 mmol) in N,N-dimethylformamide (10 ml) is heated at 75° C. for 19.5 hours. After cooling to ambient temperature, the mixture is diluted with ethyl acetate and filtered. The filtrate is washed with saturated aqueous sodium bicarbonate, then washed 2× with water, dried over magnesium sulfate, filtered, concentrated in vacuo, and purified on Silica gel (1:1 ethyl acetate/hexanes) to give 4-nitro-(2-Hydroxyethoxy)benzene (1.25 g).

Aufarbeitung

  1. temperatureAfter cooling to ambient temperature
  2. filtrationfiltered
  3. washThe filtrate is washed with saturated aqueous sodium bicarbonate
  4. washwashed 2× with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. custompurified on Silica gel (1:1 ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-fd20272e33df4231ae4b618936dbe6e6
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06743817B2

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