Hydrochloric Acid → 4-Butoxybenzoic acid

Participants

Reaction Steps

(Scheme 1, Compound B) To a solution of ethyl 4-butoxybenzoate (2.0 g, 9.6 mmol) in EtOH (30 mL) was added NaOH (10 N, 6 mL, 60 mmol). The resulting mixture was stirred at room temperature for 3 hours, diluted with H2O (30 mL), acidified to about pH 1.0 using HCl (6N). The precipitates were filtered off by filter paper, washed by H2O and hexanes. This compound was obtained as a white solid. (1.63 g, 9.1 mmol, 94% yield). 1H NMR (DMSO-d6) δ 12.59 (br. s, 1H), 7.88 (d, 2H, J=9.5 Hz), 6.97 (d, 2H, J=9.5 Hz), 4.01 (t, 2H, J=6.5 Hz), 1.68 (m, 2H), 1.42 (m, 2H), 0.91 (t, 3H, J=6.5 Hz); 13C NMR (DMSO): 166.9, 162.2, 131.2, 122.7, 114.0, 67.3, 30.5, 18.6 and 13.5; Mass Spec.: 195.17 (MH+).

Provenance & Evidence