Acetic Acid → 2-(2,2,2-Trifluoroethoxy)-3-chlorophenylacetic acid

HRID 1740605Notes

Reaction equation

HRID 1740605 reaction equation
[F:1][C:2]([F:16])([F:15])[CH2:3][O:4][C:5]1[C:10]([Cl:11])=[CH:9][CH:8]=[CH:7][C:6]=1CC#N.Cl.[C:18]([OH:21])(=[O:20])[CH3:19]>>[F:16][C:2]([F:1])([F:15])[CH2:3][O:4][C:5]1[C:10]([Cl:11])=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:19][C:18]([OH:21])=[O:20]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 540256162-(2,2,2-Trifluoroethoxy)-3-chlorophenylacetonitrile

Product 1

HCID 539993942-(2,2,2-Trifluoroethoxy)-3-chlorophenylacetic acid

Procedure

2-(2,2,2-trifluoroethoxy)-3-chlorophenyl-acetonitrile (1.2 g, 5.1 mmol) from Step 3 above was refluxed in a 2:1 mixture of acetic acid and concentrated aqueous HCl (25 mL) for 12 h. The solvents were removed under reduced pressure and the residue was partitioned between EtOAc and water. The organic phase was washed with water, dried (MgSO4), filtered, and the solvent was removed under reduced pressure to give 2-(2,2,2-trifluoroethoxy)-3-chlorophenylacetic acid as an oil.

Workup

  1. customThe solvents were removed under reduced pressure
  2. customthe residue was partitioned between EtOAc and water
  3. washThe organic phase was washed with water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-8a547bdc1cf0432c8566d85090a97660
Source dataset
uspto-grants-1999_10
Patent number
US05968938

Reaction notes

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