Hydroquinone → 4-(2-Bromoethoxy)phenol

HRID 133778Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 133778
C(=O)([O-])[O-].[K+].[K+].[C:7]1([CH:14]=[CH:13][C:11]([OH:12])=[CH:10][CH:9]=1)[OH:8].[Br:15][CH2:16][CH2:17]Br>CC(C)=O>[Br:15][CH2:16][CH2:17][O:8][C:7]1[CH:14]=[CH:13][C:11]([OH:12])=[CH:10][CH:9]=1

Komponenten

5

Edukt 3

HCID 785HydroquinoneHCID 78391,2-DibromoethaneHCID 11430Potassium Carbonate

Produkt 1

HCID 128339324-(2-Bromoethoxy)phenol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

Potassium carbonate (7.53 g, 0.05448 mol) was added to the acetone solution (50 ml) of hydroquinone (2.00 g, 0.01816 mol) and 1,2-dibromoethane (3.39 g, 0.01805 mol). The mixture was heated at reflux for 6 h under nitrogen. The resulting mixture was filtered, water was added and pH was adjusted to 2-3. The mixture was extracted with ethyl acetate. The extracts were washed with water, dried over anhydrous Na2SO4, filtered and evaporated. The crude product was purified by flash chromatography on silica gel, using heptane/ethyl acetate as a gradient eluent (95:5-70:30) to afford the pure desired compound as white crystals. 1H NMR (400 MHz, DMSO-d6): 3.74 (2H, t, 3J=5.5 Hz), 4.19 (2H, t, 3J=5.5 Hz), 6.67 (2H, d, 3J=8.9 Hz), 6.78 (2H, d, 3J=8.9 Hz), 8.95 (1H, s, —OH).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 6 h under nitrogen
  3. filtrationThe resulting mixture was filtered
  4. additionwater was added
  5. extractionThe mixture was extracted with ethyl acetate
  6. washThe extracts were washed with water
  7. dry with materialdried over anhydrous Na2SO4
  8. filtrationfiltered
  9. customevaporated
  10. customThe crude product was purified by flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-490a213bb08d4717aa0a56be5895db94
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07390923B2

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