Hydrochloric Acid → 4-(2-Chlorophenoxy)butanoic acid

Participants

Reaction Conditions

Reaction Steps

A 500 mL 3-neck round bottom flask equipped with a magnetic stirrer bar and a reflux condenser was charged with 12.88 g (100 mmol) of 2-chlorophenol, 22.54 g (110 mmol) of ethyl 4-bromobutyrate, 16.59 g, 120 mmol potassium carbonate and 350 mL of 2-butanone. The slurry was heated to reflux. After stirring for 21 hr at reflux, the reaction mixture was cooled to 25° C., filtered and concentrated. The residue was taken up in 400 mL of water and treated with 100 mL of 2N aqueous sodium hydroxide (200 mmol). The reaction mixture was heated to reflux for 120 min and cooled to 25° C. The resulting solution was acidified with aqueous 105 ml of 2N hydrochloric acid. The resulting white solid was isolated by filtration by washing with hexanes to yield 20.68 g of 4-(2-Chlorophenoxy)butanoic acid. Mp 85-87° C. Combustion analysis: Found: C, 55.97; H, 5.13%; Cl, 16.55%; C10H11ClO3 requires C, 55.96; H, 5.17%; Cl, 16.52%; 1H NMR (d6-DMSO): δ 12.1, bs, 1H (COOH); δ 7.42, dd, 1H, (H ortho to Cl); δ 7.29, t, 1H (H para to Cl); δ 7.13, d, 1H, (H ortho to OR); δ 6.95, t, 1H (H para to OR); δ 4.07, t, 2H, (CH2 α to O); δ 2.44, t, 2H (CH2 α to COOH); δ 1.98, p, 2H (CH2 β to ArO and COOH).

Provenance & Evidence