Hydrochloric Acid → HCID 59192512, compound

Participants

Reaction Steps

A mixture of zinc pieces (11.4 g), mercuric chloride (3.0 g), concentrated hydrochloric acid (4.6 mL) and water (140 mL) was stirred at room temperature for 5 minutes. The solvent was then decanted off. To the solid, were added concentrated hydrochloric acid (41 mL), water (18.6 mL), toluene (23 mL) and 4-(4-chloro-3-fluoro-2-hydroxy-phenyl)-4-oxo-butyric acid (8.6 g, 35 mmol). The resulting mixture was heated at reflux for 2 days, with the addition of concentrated hydrochloric acid in 12 hour intervals. The reaction mixture was cooled and extracted with ether (50 mL×3). The collected organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to give pure 4-(4-chloro-3-fluoro-2-hydroxy-phenyl)-butyric acid (6.0 g, 74%), which was used in the next step without further purification. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.74 (dt, 2H), 2.20 (t, J=7.40 Hz, 2H), 2.57 (t, J=7.56 Hz, 2H), 6.87-6.92 (m, 2H), 9.90 (br s, 1H), 12.03 (br s, 1H).

Provenance & Evidence