Hydrochloric Acid → 4-(2-Phenylethynyl)benzoic acid

Participants

Reaction Steps

To a solution of ethyl 4-(phenylethynyl)benzoate (7.81 g, 31.2 mmol) in THF (80 mL) was added MeOH (15 mL) and a solution of LiOH (5.24 g, 124 mmol) in water (15 mL). The reaction was stirred at room temperature and for 4 h. The reaction was acidified with 1 N HCl (50 mL), and 4-(phenylethynyl)benzoic acid was isolated (5.78 g, 83%) as a white solid; 1H-nmr (400 MHz, CDCl3) δ 8.11 (d, J=8.0 Hz, 2H), 7.75-7.68 (m, 1H), 7.64 (d, J=8.0 Hz, 2H), 7.62-7.56 (m, 2H), 7.52-7.47 (m, 1H), 7.43-7.36 (m, 3H); LC (275 nM) 5.12 min (>98%); MS (ESI) m/z=222.9.

Provenance & Evidence