Formic Acid → 2-Adamantanecarboxylic acid

Participants

Reaction Conditions

Reaction Steps

Concentrated sulfuric acid (50 mL) and carbon tetrachloride (100 mL) were combined, cooled to 0° C. and vigorously stirred. Adamantan-2-ol (451 mg) was dissolved in 96% formic acid (6 mL) and the solution was added to the sulfuric acid over 1 hour. The reaction continued to stir at 0° C. for 90 min after which it was added to 300 mL of ice. The layers were separated and the aqueous layer was extracted with 50 mL carbon tetrachloride (2×). The organic layers were combined and extracted with 1N NaOH. The aqueous portion was extracted with methylene chloride (4×) then acidified with 5N HCl. The solution turned white and was cooled on ice. Filtration provided the desired adamantane-2-carboxylic acid (contaminated with about 5% adamantane-1-carboxylic acid) as a white powder.

Provenance & Evidence