4-Hydroxybenzenesulfonic acid → Sodium 4-(4-fluorobenzyloxy)benzenesulfonate

Participants

Reaction Steps

To a solution of 4-hydroxybenzenesulfonic acid (5.13 grams, 22.1 mmole) in 1 N aqueous sodium hydroxide solution (23 mL) was added a solution of 4-fluorobenzylbromide (3.3 mL, 26.5 mmole) in ethanol (20 mL). The resulting mixture was heated at reflux for 2 days. Upon cooling and standing, a white solid precipitated. The precipitated product, sodium 4-(4-fluorobenzyloxy)benzenesulfonate, 4.95 grams (74%) was collected by filtration washing with ethyl acetate and diethyl ether.

Provenance & Evidence