Methylparaben → Methyl 4-(benzyloxy)benzoate

Participants

Reaction Conditions

Reaction Steps

To a solution of 15.2 g of methyl4-hydroxybenzoate (100 mmol) in 125 mL of N,N-dimethylformamide was added under stirring 33.13 g of potassium carbonate (240 mmol). Then 17.45 g of benzyl bromide (102 mmol) was added within 5 minutes. The mixture was stirred at 25° C. using a water bath. The reaction was complete after 3 hours. The reaction mixture was poured into a mixture of 180 g of ice and 200 mL of ethyl acetate. After extraction, the aqueous phase was separated and extracted with three portions of 80 mL of ethyl acetate. The organic phase was washed with two portions of 150 mL of water, combined, dried (MgSO4) and partially concentrated to give a thick suspension. 60 mL of pentane was added and the suspension was stirred during 2 hours at room temperature. The crystalline methyl 4-benzyloxybenzoate was collected on a filter, washed with pentane and dried.

Provenance & Evidence