Acetone → 2,6-Diallyl4-benzyloxyphenol

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:16](Br)[CH:17]=[CH2:18].C([O-])([O-])=O.[K+].[K+].[CH3:26][C:27]([CH3:29])=O>>[CH2:16]([C:11]1[CH:10]=[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:14]=[C:13]([CH2:29][CH:27]=[CH2:26])[C:12]=1[OH:15])[CH:17]=[CH2:18]

Participants

Reactant 4

HCID 180Acetone

HCID 7638Monobenzone

HCID 7841Allyl bromide

HCID 11430Potassium Carbonate

Product 1

HCID 219859512,6-Diallyl4-benzyloxyphenol

Procedure

To a solution of starting 4-benzyloxyphenol (20 g) in acetone (800 mL) were added allylbromide (50 mL) and K2CO3 (60 g). The reaction mixture was refluxed overnight. After cooling to the room temperature, the insoluble materials were removed by filtration. The filtrate was concentrated in vac. The residue was partitioned between ethyl ether (500 mL) and 2N aqueous NaOH (200 mL). The organic layer was washed with water and brine, dried over anhydrous MgSO4, filtered, and concentrated in vac. to give the desired product.