Trifluoromethanesulfonic acid → 5-Phenyladamantan-2-one

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of compound 5-hydroxyadamantan-2-one (10.0 g, 60.2 mmol) in benzene (180 mL) was added trifluoromethanesulfonic acid (5.3 mL, 60.2 mmol) over a period of 30 minutes at r.t. After stirring the reaction mixture for 5 minutes at r.t, it was refluxed for 4 h. The reaction mixture was cooled to 0° C. and sat. aq. NaHCO3 (76 mL) was added over a period of 30 minutes. Two layers were separated, the aqueous layer was extracted with ether and the combined layer was washed with water and brine, dried over anhydrous Na2SO4, and the solvent was evaporated under reduced pressure to obtain 5-Phenyladamantan-2-one (10.5 g) as a white solid in 80% yield. M.R: 53.8-60.9° C. m/z (M+1) 227; IR (cm−1): 2921, 2853, 1717, 1446, 1060, 758, 698. 1H NMR (CDCl3) 300 MHz δ 7.37-7.30 (m, 4H), 7.26-7.19 (m, 1H), 2.70-2.63 (m, 2H), 2.30-2.0 (m, 11H). 13C NMR (CDCl3) 75 MHz δ 217.8, 147.8, 128.3 (2C), 126.1, 124.6 (2C), 46.9 (2C), 44.3 (2C), 41.9, 35.9, 38.4 (2C), 28.0.

Provenance & Evidence