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

HRID 1167816Notes

Reaction equation

HRID 1167816 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

5

Reactant 2

HCID 229943582-(4-Chloro-2-trifluoromethylphenyl)-ethanolHCID 131709961Jones' reagent

Product 1

HCID 32777474-Chloro-2-(trifluoromethyl)phenylacetic acid

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 1118Sulfuric AcidSolvent

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).

Workup

  1. additionthe mixture was poured onto Et2O/H2O
  2. customthe layers were separated
  3. washThe organic layer was washed with H2O and brine
  4. dry with materialdried (MgSO4)
  5. customthe solvent was removed in vacuo
  6. customThe resultant orange solid was crystallized from hexane and heptane

Sources & evidence

ORD record
ord-11adbdf3f6f243b59cf5ab1c61993171
Source dataset
uspto-grants-2003_09
Patent number
US06620838B1

Reaction notes

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