Formic Acid → Methyl 4-oxoadamantane-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

A solution of 5-hydroxy-2-adamantanone (2.0 g, 12.0 mmol) in 99% formic acid (12 mL) was added dropwise with vigorous gas evolution over 40 minutes to a rapidly stirred 30% oleum solution (48 mL) heated to 60° C. (W. J. le Noble, S. Srivastava, C. K. Cheung, J. Org. Chem. 1983, 48, 1099-1101.). Upon completion of addition, more 99% formic acid (12 mL) was slowly added over the next 40 minutes. The mixture was stirred another 60 minutes at 60° C. and then slowly poured into vigorously stirred methanol (100 mL) cooled to 0° C. The mixture was allowed to slowly warm to 23° C. while stirring for 2 hours and then concentrated in vacuo. The residue was poured onto ice (30 g), and methylene chloride (100 mL) was added. The layers were separated, and the aqueous phase was extracted twice more with methylene chloride (100 mL aliquots). The combined methylene chloride solutions were concentrated in vacuo to 50 mL, washed with brine, dried over N2SO4, filtered, and concentrated in vacuo to provide the title compound as a pale yellow solid (2.5 g, 99% crude).

Provenance & Evidence