Water → Dimethyl 5-bentyloxy-isophthalate

Participants

Reaction Steps

To a solution of dimethyl 5-hydroxyisophthalate (50.0 g, 238 mmol) in N,N-dimethylformamide (500 mL), benzyl bromide (29.5 mL, 248 mmol) was added dropwise in the presence of potassium carbonate (42.4 g, 307 mmol), and the reaction mixture was stirred for 2 hours at room temperature, followed by addition of water thereto. The resultant mixture was extracted with diethyl ether. The resultant organic layer was washed sequentially with water and saturated brine and dried over sodium sulfate anhydrate. The solvent was removed under reduced pressure, to thereby yield a solid. The solid was crystallized from diethyl ether, to thereby yield 68.9 g of dimethyl 5-benzyloxyisophthalate as colorless needles (yield 96%).

Provenance & Evidence