Methyl (3'-benzyloxy-4'-methoxybiphenyl-3-yl)acetate → Methyl (3'-hydroxy-4'-methoxybiphenyl-3-yl)acetate

HRID 2247438Notes

Reaction equation

HRID 2247438 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][C:24]([O:26][CH3:27])=[O:25])[CH:18]=2)[CH:12]=[CH:13][C:14]=1[O:15][CH3:16])C1C=CC=CC=1.[H][H]>C(OCC)(=O)C.C(O)C.[C].[Pd]>[OH:8][C:9]1[CH:10]=[C:11]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][C:24]([O:26][CH3:27])=[O:25])[CH:18]=2)[CH:12]=[CH:13][C:14]=1[O:15][CH3:16]

Participants

6

Reactant 2

HCID 59219255Methyl (3'-benzyloxy-4'-methoxybiphenyl-3-yl)acetateHCID 178418361HCID 178418361, compound

Product 1

HCID 59219199Methyl (3'-hydroxy-4'-methoxybiphenyl-3-yl)acetateYield 95.6%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.35 g of Methyl (3′-benzyloxy-4′-methoxybiphenyl-3-yl)acetate was dissolved in a mixed solvent of 10 ml of ethyl acetate and 30 ml of ethanol, then 500 mg of 10% palladium-carbon was added thereto, and the mixture was stirred overnight in a hydrogen atmosphere. The reaction mixture was filtered through Celite, and the filtrate was concentrated. The residue was purified by silica gel column chromatography, to give 970 mg of the title compound in the 3:1 hexane-ethyl acetate fraction.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9969b9a89e8b45bdb1b159b4e9df98f6
Source dataset
uspto-grants-2010_03
Patent number
US07687664B2

Reaction notes

Loading…