Tert-butyl 4-(benzyloxy)benzoate → tert-Butyl 4-hydroxybenzoate

HRID 1840941

Reaction equation

HRID 1840941 reaction equation
[C:1]([O:5][C:6](=[O:21])[C:7]1[CH:12]=[CH:11][C:10]([O:13]CC2C=CC=CC=2)=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2]>[Pd].C(O)C>[C:1]([O:5][C:6](=[O:21])[C:7]1[CH:8]=[CH:9][C:10]([OH:13])=[CH:11][CH:12]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 53864121Tert-butyl 4-(benzyloxy)benzoate

Product 1

HCID 117640tert-Butyl 4-hydroxybenzoateYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

0.36 g of 10% palladium on activated carbon were added to a solution of 1.2 g (4.3 mmol) of 4-benzyloxy-benzoic acid tert-butyl ester in 45 mL of ethanol and this mixture was hydrogenated at 20 psi for 3 hours. After filtering over celite and removing the solvent under reduced pressure 0.79 g (95% yield) of 4-hydroxy-benzoic acid tert-butyl ester were obtained.

Workup

  1. filtrationAfter filtering over celite

Sources & evidence

ORD record
ord-088307d29382438e849941b901475049
Source dataset
uspto-grants-2004_01
Patent number
US06683096B2

Linked notes

Loading…