Acetone → 4-(Allyloxy)phenol

HRID 1370826

Reaction equation

HRID 1370826 reaction equation
[CH2:1](I)[CH:2]=[CH2:3].[C:5]1([CH:12]=[CH:11][C:9]([OH:10])=[CH:8][CH:7]=1)[OH:6].C([O-])([O-])=O.[K+].[K+].CC(C)=O>>[CH2:1]([O:6][C:5]1[CH:12]=[CH:11][C:9]([OH:10])=[CH:8][CH:7]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 4

HCID 180AcetoneHCID 785HydroquinoneHCID 11166Allyl iodideHCID 11430Potassium Carbonate

Product 1

HCID 17138834-(Allyloxy)phenolYield 41.2%

Conditions

Temperature
40 °C

Procedure

Allyl iodide (8.2 mL, 89 mmoles) was added to a solution of hydroquinone (7.84 g, 71.2 mmoles) and K2CO3 (19.7 g, 142.4 mmoles) in acetone (102 mmoles). The resulting mixture was heated to 40° C. overnight and concentrated under reduced pressure. The crude products were filtered through a pad of silica with 1:1 hexanes:ethyl acetate. The residue was purified by flash chromatography on a prepacked Biotage column (hexane to 1:1 hexane:ethyl acetate) on silica gel to provide the title compound (4.40 g, 41%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. filtrationThe crude products were filtered through a pad of silica with 1:1 hexanes
  3. customThe residue was purified by flash chromatography on a prepacked Biotage column (hexane to 1:1 hexane:ethyl acetate) on silica gel

Sources & evidence

ORD record
ord-27744a5ea8714d8d86bfbc104de5ee09
Source dataset
uspto-grants-2003_06
Patent number
US06583180B2

Linked notes

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