Acetic Acid → HCID 54304074, compound

HRID 2289364Notes

Reaction equation

HRID 2289364 reaction equation
[F:1][C:2]([F:16])([F:15])[CH2:3][O:4][C:5]1[CH:10]=[C:9]([F:11])[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[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:6]=1[CH2:19][C:18]([OH:21])=[O:20]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 54447024HCID 54447024, compound

Product 1

HCID 54304074HCID 54304074, compound

Procedure

To a stirred solution of 2-(2,2,2-trifluoroethoxy)-4-fluorophenylacetonitrile (0.60 g, 2.7 mmol) from Step 4 above in acetic acid (10 mL) was added 12 N aqueous HCl (5 mL). The mixture was refluxed for 4 h. The solvents were removed under reduced pressure and the residue was partitioned between EtOAc (100 mL) and water (2×50 mL). The organic phase was dried (MgSO4), filtered, and the solvent was removed under reduced pressure to give 2-(2,2,2-trifluoroethoxy)-4-fluorophenylacetic acid as an amorphous solid (HPLC retention time=7.5 min (method A)).

Workup

  1. temperatureThe mixture was refluxed for 4 h
  2. customThe solvents were removed under reduced pressure
  3. customthe residue was partitioned between EtOAc (100 mL) and water (2×50 mL)
  4. dry with materialThe organic phase was dried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-e208fab1888c4e65a1659e20696e7cb1
Source dataset
uspto-grants-2000_07
Patent number
US06090805

Reaction notes

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