[Cl:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].[C:16]1([Li])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CCOCC.C1CCCCC1.CCOCC>[Cl:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[C:4]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[OH:5]To a stirred, ice-cooled solution of 2-chlorobenzophenone (21.6 g, 100 mmol) in 150 mL of dry Et2O under N2 was added 60 mL (120 mmol) of 2.0 M phenyllithium solution in cyclohexane-Et2O (7:3), keeping T<15° C. After stirring for a further 1 h at 15° C., the solution was poured onto crushed ice and extracted with Et2O. The organic solution was washed with 0.2 M H2SO4, water (until neutral), brine, dried (MgSO4), filtered and concentrated. The residue was recrystallized from hexanes containing a few per cent EtOAc to give 23.1 g (78%) of (2-chlorophenyl)diphenylmethanol as an off-white solid.
Loading…
