Hydroquinone → 4-(Allyloxy)phenol

HRID 613405

Reaktionsgleichung

Reaktionsgleichung von HRID 613405
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].C(=O)([O-])[O-].[K+].[K+].[CH2:15](Br)[CH:16]=[CH2:17]>CN(C=O)C>[CH2:17]([O:2][C:1]1[CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[CH:16]=[CH2:15]

Komponenten

5

Edukt 3

HCID 785HydroquinoneHCID 7841Allyl bromideHCID 11430Potassium Carbonate

Produkt 1

HCID 17138834-(Allyloxy)phenol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of hydroquinone (33.00 g, 0.30 mol) and potassium carbonate (45.6 g, 0.33 mol) in dry DMF (250 mL) was stirred at 40° C. for minutes. Allyl bromide (5.20 mL, 0.06 mol) was added and the reaction was stirred overnight. The reaction mixture was partitioned between ethyl acetate and 0.2N HCl. The organic layer was washed twice with water, then dried over sodium sulfate. The organic layer was filtered and evaporated to an oil which was chromatographed over silica gel with hexane/ethyl acetate (4:1) to afford 4-allyloxyphenol.

Aufarbeitung

  1. customThe reaction mixture was partitioned between ethyl acetate and 0.2N HCl
  2. washThe organic layer was washed twice with water
  3. dry with materialdried over sodium sulfate
  4. filtrationThe organic layer was filtered
  5. customevaporated to an oil which
  6. customwas chromatographed over silica gel with hexane/ethyl acetate (4:1)

Quellen und Nachweise

ORD-Eintrag
ord-8bf6c6150ef04d398fbae183c9b71ec1
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US06008237

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