Hydroquinone → 4-(Allyloxy)phenol

HRID 613405

Reaction equation

HRID 613405 reaction equation
[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]

Participants

5

Reactant 3

HCID 785HydroquinoneHCID 7841Allyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 17138834-(Allyloxy)phenol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-8bf6c6150ef04d398fbae183c9b71ec1
Source dataset
uspto-grants-1999_12
Patent number
US06008237

Linked notes

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