Iodoethane → 5-Chloro-2-ethoxybenzoic acid

Participants

Reaction Steps

To a mixture of 5-chlorosalicylic acid (20.0 g, 116 mmol) and potassium carbonate (48.4 g, 350 mmol) in acetonitrile (300 ml) was added iodoethane (24.0 ml, 299 mmol). The mixture was heated under reflux for 24 hours. After cooling to room temperature, the mixture was filtered through a pad of celite under suction and the filtrate was concentrated under reduced pressure. The residue was dissolved in ethyl acetate (200 ml). The solution was washed with water (100 ml), washed with aqueous sodium hydroxide solution (1 M, 2×100 ml), dried over sodium sulfate, and concentrated under reduced pressure. The residue was dissolved in ethanol (200 ml) and a solution of sodium hydroxide (10.7 g, 268 mmol) in water (50 ml) was added. The mixture was heated under reflux for 90 minutes. After cooling to room temperature, the mixture was concentrated under reduced pressure. The residue was dissolved in water (100 ml) and the solution was washed with diethyl ether (2×50 ml). The solution was adjusted to pH 2 by the careful addition of concentrated hydrochloric acid. After 60 minutes, the solid was filtered and dried under reduced pressure to provide 5-chloro-2-ethoxybenzoic acid (20.4 g, 90% yield).

Provenance & Evidence