Acetic Acid → HCID 18700158, compound

HRID 2289321Notes

Reaction equation

HRID 2289321 reaction equation
[F:1][C:2]([F:16])([O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1CC#N)[CH:3]([F:5])[F:4].Cl.[C:18]([OH:21])(=[O:20])[CH3:19]>>[F:1][C:2]([F:16])([O:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=1[CH2:19][C:18]([OH:21])=[O:20])[CH:3]([F:4])[F:5]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 18700173HCID 18700173, compound

Product 1

HCID 18700158HCID 18700158, compound

Procedure

2-(1,1,2,2-Tetrafluoroethoxy)phenylacetonitrile (0.49 g, 2.4 mmol) from Step 2 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-(1,1,2,2-tetrafluoroethoxy)phenylacetic acid as an amorphous solid (HPLC retention time=7.7 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-ca4cd2927d0044fdbc1572bd5c9ad713
Source dataset
uspto-grants-2000_07
Patent number
US06090805

Reaction notes

Loading…