Trifluoromethanesulfonic acid → 1-Methyladamantane

Participants

Reaction Conditions

Reaction Steps

A mixture of 7.5 g (0.05 mole) of tricyclo[5.3.1.03,8 ]-undecane (II) and 76 g (0.5 mole) of trifluoromethanesulfonic acid was heated at 80°C. for 30 hours under agitation. The reaction mixture was allowed to cool and then poured over 200 ml of ice water. The organic layer was separated and the water layer was extracted with methylene chloride. The methylene chloride extract was combined with the organic layer, and the mixture was washed with a saturated aqueous solution of sodium hydrogencarbonate and then with water, and dried over anhydrous sodium sulfate. Methylene chloride was distilled off and the residue was sublimed to obtain 6.8 g (yield: 90 wt.%) of 1-methyladamantane (II). All of the IR, NMR and MS spectra of the product were in agreement with those of the authentic sample.

Provenance & Evidence