Water → HCID 18700164, compound

HRID 2289347Notes

Reaction equation

HRID 2289347 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11]C)=[O:10])=[C:4]([O:13][CH2:14][C:15]([F:18])([F:17])[F:16])[CH:3]=1.O.[Li+].[OH-]>C1COCC1>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[C:4]([O:13][CH2:14][C:15]([F:16])([F:17])[F:18])[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 18700130HCID 18700130, compound

Product 1

HCID 18700164HCID 18700164, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 4-hydroxy-2-(2,2,2-trifluoroethoxy)phenylacetate (1.3 g, 4.8 mmol) from Step 4 above in THF (15 mL) was added water (3 mL) and LiOH (0.62 g, 15 mmol). The mixture was stirred at ambient temperature for 6 h and the solvents were removed under reduced pressure. The residue was partitioned between CH2Cl2 and aqueous citric acid. The organic phase was dried (MgSO4), filtered, and the solvent was removed under reduced pressure to give 4-hydroxy-2-(2,2,2-trifluoroethoxy)phenylacetic acid as an amorphous solid (HPLC retention time=13.2 min (method D)).

Workup

  1. customthe solvents were removed under reduced pressure
  2. customThe residue was partitioned between CH2Cl2 and aqueous citric acid
  3. dry with materialThe organic phase was dried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-e204fdfe873d4b14a99fbc9e7365e620
Source dataset
uspto-grants-2000_07
Patent number
US06090805

Reaction notes

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