5-Methoxy-3-phenyl-3H-isobenzofuran-1-one → 2-Benzyl-4-methoxybenzoic acid

HRID 985148Notes

Reaction equation

HRID 985148 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[O:7][CH:6]2[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(O)C.[Pd]>[CH2:6]([C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:11]=[CH:10][C:9]=1[C:8]([OH:12])=[O:7])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 1

HCID 131723595-Methoxy-3-phenyl-3H-isobenzofuran-1-one

Product 1

HCID 225559782-Benzyl-4-methoxybenzoic acidYield 91.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 9 (12.0 g, 50 mmol) in ethanol was added 10% palladium on carbon (1.5 g). The resulting suspension was hydrogenated at 60 psi for 18 h. Filtration through celite followed by removal of the solvent in vacuo gave 10 as a white solid (11.0 g, 45.5 mmol, 91.1%).

Workup

  1. filtrationFiltration through celite
  2. customfollowed by removal of the solvent in vacuo

Sources & evidence

ORD record
ord-3f5122da7540414fbce02b3069b1e3fe
Source dataset
uspto-grants-2005_03
Patent number
US06870055B2

Reaction notes

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