Cyclohexaneacetic acid → HCID 53876855, compound

Participants

Reaction Steps

To a solution of cyclohexylacetic acid (10 g, 70 mmol), in 100 ml of CCl4 was added red phosphorus (6.32 g, 204 mmol). The mixture was heated to reflux and bromine (70.7 ml, 1.38 mmol) was added over 3 hours dropwise through the condenser via addition fimnel. The reaction was heated at reflux for 5 hours before it was quenched slowly with water then washed with 10% Na2SO4, water, then into NaHCO3. The sodium bicarbonate solution was brought to acidic pH using 1 N HCl. The solid was collected and the aqueous filtrate was extracted into CHCl3, washed with saturated Na2HSO4 solution then with water. The organic layer was dried over Na2SO4, filtered and concentrated and combined with solid collected earlier to provide 3.22 g 2-bromo cyclohexyl acetic acid as a white solid. Yield 21%; MS: 219.1 (M−H)−

Provenance & Evidence