Hydrochloric Acid → (1S,2R)-2-(4-Pyridinylmethyl)cyclohexanecarboxylic acid

Participants

Reaction Steps

A mixture of 8.5 M hydrochloric acid (10.5 mL), Zn (5.57 g, 85.2 mmol), and HgCl2 (0.557 g, 2.1 mmol) was stirred for 15 min, and then (1S,2R)-2-(4-pyridylcarbonyl)cyclohexanecarboxylic acid (0.30 g, 1.3 mmol) was added. The reaction mixture was stirred at reflux for 20 h, and then diluted with 10% citric acid (75 mL), and then adjusted to pH=4 by addition of 10 M NaOH. The reaction mixture was extracted with ethyl acetate, washed with sat. brine, dried over MgSO4, filtered, and evaporated to give (1S,2R)-2-(4-pyridylmethyl)-cyclohexanecarboxylic acid, as a white semi-solid (0.25 g, 90%).

Provenance & Evidence