3-(Benzyloxy)-4-(trifluoromethyl)benzoic acid → 3-hydroxy-4-(trifluoromethyl)benzoic Acid

HRID 1755113Notes

Reaction equation

HRID 1755113 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=1[C:18]([F:21])([F:20])[F:19])[C:12]([OH:14])=[O:13])C1C=CC=CC=1.[H][H]>[Pd].CO.C(OCC)(=O)C>[OH:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=1[C:18]([F:19])([F:20])[F:21])[C:12]([OH:14])=[O:13]

Participants

5

Reactant 2

HCID 167478443-(Benzyloxy)-4-(trifluoromethyl)benzoic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 109436363-hydroxy-4-(trifluoromethyl)benzoic AcidYield 86%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

10% Pd/C (590 mg) was added to 3-benzyloxy-4-trifluoromethyl-benzoic acid in a methanol-ethyl acetate mixed solvent (1:1), and the mixture was stirred at room temperature for two days in a hydrogen atmosphere. The reaction solution was filtered through celite, and the filtrate was then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane-ethyl acetate) to give 3-hydroxy-4-trifluoromethyl-benzoic acid (582 mg, 86%).

Workup

  1. filtrationThe reaction solution was filtered through celite
  2. concentrationthe filtrate was then concentrated under reduced pressure
  3. customThe resulting residue was purified by silica gel column chromatography (n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-35f5cb688ced4673951434074d249c21
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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