4-Hydroxybenzaldehyde → 4-(Allyloxy)benzaldehyde

Participants

Reaction Conditions

Reaction Steps

A solution of allyl bromide (5.94 mL, 68.78 mmol) in acetone (20 mL) was added, over a period of 20 min, to a mixture of 4-hydroxybenzaldehyde (8.00 g, 65.50 mmol) and K2CO3 (9.96 g, 72.06 mmol) in acetone (100 mL) cooled at 0° C. The mixture was allowed to reach room temperature and stirred for 60 h. After removal of the solvent, the crude residue was dissolved in EtOAc (100 mL) and washed twice with a mixture of water (100 mL) and NaOH (10% aqueous solution, 10 mL). The organic layer was dried over anhydrous Na2SO4 and filtered. After removal of the solvent, 10.00 g of 4-(allyloxy)benzaldehyde were obtained [Rf=0.5 (10% EtOAc/Hexanes), pale brown oil, 94% yield]

Provenance & Evidence