Trifluoromethanesulfonic acid → 5-Phenyladamantan-2-one

HRID 1015502Notes

Reaction equation

O[C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([C:5]3=[O:12])[CH2:3]1)[CH2:9]2.FC(F)(F)S(O)(=O)=O.C([O-])(O)=O.[Na+]>C1C=CC=CC=1>[C:2]1([C:2]23[CH2:11][CH:6]4[CH2:7][CH:8]([CH2:10][CH:4]([C:5]4=[O:12])[CH2:3]2)[CH2:9]3)[CH:11]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

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.

Workup

temperaturewas refluxed for 4 h
customTwo layers were separated
extractionthe aqueous layer was extracted with ether
washthe combined layer was washed with water and brine
dry with materialdried over anhydrous Na2SO4
customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-ed8c27752d114de5805cc694eff4272c
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07985759B2

Reaction notes

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