Acetic Acid → 2-[2-(Trifluoromethoxy)phenyl]acetic acid

HRID 2289318Notes

Reaction equation

HRID 2289318 reaction equation
[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1CC#N.Cl.[C:16]([OH:19])(=[O:18])[CH3:17]>>[F:1][C:2]([F:13])([F:14])[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:17][C:16]([OH:19])=[O:18]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 27773212-(Trifluoromethoxy)phenylacetonitrile

Product 1

HCID 27773132-[2-(Trifluoromethoxy)phenyl]acetic acid

Procedure

2-Trifluoromethoxyphenylacetonitrile (0.49 g, 2.6 mmol) from Step 3 above was refluxed for 3 h in a 1:1 mixture of acetic acid and concentrated aqueous HCl. The solvents were removed under reduced pressure. The residue was partitioned between EtOAc (75 mL) and water (2×25 mL). The organic phase was separated, dried (MgSO4), filtered, and evaporated under reduced pressure to give 2-trifluoromethoxyphenylacetic acid as an amorphous solid (HPLC retention time=6.8 min (method A)).

Workup

  1. customThe solvents were removed under reduced pressure
  2. customThe residue was partitioned between EtOAc (75 mL) and water (2×25 mL)
  3. customThe organic phase was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-c6fa9a1168d34d4f8f289bb55aa9ec2f
Source dataset
uspto-grants-2000_07
Patent number
US06090805

Reaction notes

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