Methyl 4-(2-benzyloxybenzyl)benzoate → Methyl 4-(2-hydroxybenzyl)benzoate

HRID 554533Notes

Reaction equation

HRID 554533 reaction equation
[CH3:1][O:2][C:3](=[O:25])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:17]CC2C=CC=CC=2)=[CH:6][CH:5]=1>CO.[OH-].[Pd+2].[OH-]>[CH3:1][O:2][C:3](=[O:25])[C:4]1[CH:5]=[CH:6][C:7]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[OH:17])=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 21909320Methyl 4-(2-benzyloxybenzyl)benzoate

Product 1

HCID 21909287Methyl 4-(2-hydroxybenzyl)benzoateYield 96%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-(2-benzyloxybenzyl)benzoic acid methyl ester (2.39 g, 7.19 mmol) in methanol (70 mL), a 20% palladium hydroxide catalyst (239 mg) was added. The mixture was stirred under a hydrogen atmosphere for five hours, and then the catalyst was filtered off. The solvent was distilled under reduced pressure to obtain the title compound (1.16 g, 96%).

Workup

  1. filtrationthe catalyst was filtered off
  2. distillationThe solvent was distilled under reduced pressure

Sources & evidence

ORD record
ord-6b2966af80074a14aeeabd30cdb7dd1d
Source dataset
uspto-grants-2011_11
Patent number
US08048897B2

Reaction notes

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