Acetone → 4-(Allyloxy)phenol

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

Reactant 4

HCID 180Acetone

HCID 785Hydroquinone

HCID 11166Allyl iodide

HCID 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%).