Sulfuric Acid → 2-Hydroxybicyclo(2.2.1)heptane-2-carboxylic acid

Participants

Reaction Steps

24.1 g (367 mmol) of potassium hydroxide (85%) and 18.9 g (120 mmol) of potassium permanganate were dissolved in 84 ml of water, on ice cooling, 8.36 g (59.6 mmol) of crude 2-norbornane carboxylic acid in 84 ml of petroleum ether was added dropwise. After heating and refluxing for six hours, the mixture was stirred at room temperature for 18 hours. On ice cooling, the reaction mixture was slowly added into 120 ml of 6N sulfuric acid, 60 ml of an aqueous solution of 13.0 g of sodium bisulfite was added to the acid mixture, and the solution was stirred at room temperature for one hour. The solution was extracted with ether (100 ml×4), and the extract was dried over anhydrous magnesium sulfate and filtered. The solvent was distilled off, and 8.34 g of crude 2-hydroxy-2-norbornanecarboxylic acid was obtained. Crude yield: 90%.

Provenance & Evidence