2-(4-Chloro-2-trifluoromethylphenyl)-ethanol → 4-Chloro-2-(trifluoromethyl)phenylacetic acid

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[C:4]([C:11]([F:14])([F:13])[F:12])[CH:3]=1.CC(C)=[O:17].OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O.OS(O)(=O)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:17])=[O:10])=[C:4]([C:11]([F:12])([F:13])[F:14])[CH:3]=1

Participants

Procedure

To a solution of 2-(4-chloro-2-trifluoromethylphenyl)-ethanol in acetone (50 mL) at 0° C. was added dropwise a solution of Jones reagent (40.3 mL of a 2.67 M solution in H2SO4). After 25 min, the mixture was poured onto Et2O/H2O and the layers were separated. The organic layer was washed with H2O and brine, dried (MgSO4) and the solvent was removed in vacuo. The resultant orange solid was crystallized from hexane and heptane to furnish the title compound as a solid which showed: 1H NMR (300 MHz, CDCl3) δ 7.67 (d, 1H, J=2.0Hz), 7.51 (dd, 1H, J=2.0, 8.0Hz), 7.34 (d, 1H, J=8.0Hz), 3.84 (s, 2H).