Acetic Acid → (-)-Norcocaine

Participants

Reaction Steps

Cocaine (1.0 g, 3.29 mmol) was dissolve in a mixed solvent of acetonitrile (55 ml) and water (110 ml). Acetic acid (1 ml) was added to the mixture to form a weak acidic solution. To this solution was added an aqueous solution (42 ml) of potassium permanganate (1.06 g, 7.55 mmol) dropwise over 8 h. After the addition, the mixture was stirred overnight at room temperature. The resulting precipitate was removed by filtration, and potassium carbonate was added to the filtrate to form a basic solution. The solution was extracted with diethyl ether three times, and anhydrous potassium sulfate was added to the organic layer for dryness. The ether was distilled off under reduced pressure. The product was purified by silica gel thin-layer chromatography (eluent: ammonia-saturated chloroform) to form norcocaine (536 mg, MW=289.4, Yield: 56%).

Provenance & Evidence