Ethanol → (5-Hydroxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid ethyl ester

HRID 426305Notes

Reaction equation

HRID 426305 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH2:25][C:26]([OH:28])=[O:27])[CH:12]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=2)[CH:14]=1)C1C=CC=CC=1.[CH3:29][CH2:30]O>[Pd]>[CH2:29]([O:28][C:26](=[O:27])[CH2:25][C:11]1[CH:12]=[C:13]([C:15]2[CH:16]=[CH:17][C:18]([C:21]([F:23])([F:22])[F:24])=[CH:19][CH:20]=2)[CH:14]=[C:9]([OH:8])[CH:10]=1)[CH3:30]

Participants

4

Reactant 2

HCID 702EthanolHCID 11501912(5-Benzyloxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid

Product 1

HCID 66702499(5-Hydroxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a solution of (5-benzyloxy-4′-trifluoromethyl-biphenyl-3-yl)-acetic acid (2.5 g, 5.5 mmol) in EtOH (50 mL) was added 10% Pd/C (5% wt) and the resultant black suspension stirred under an atmosphere of H2 for 5 hours. The resultant mixture was filtered through celite and evaporated to dryness. The residue was purified by flash column chromatography (EtOAc:petroleum ether) to give (5-hydroxy-4′-trifluoromethyl-biphenyl-3-yl)-acetic acid ethyl ester as a white solid, yield 2.3 g (93%).

Workup

  1. filtrationThe resultant mixture was filtered through celite
  2. customevaporated to dryness
  3. customThe residue was purified by flash column chromatography (EtOAc:petroleum ether)

Sources & evidence

ORD record
ord-d98843f0dcff4a3c81b5f38a107fb9a6
Source dataset
uspto-grants-2012_01
Patent number
US08106236B2

Reaction notes

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