Methyl 3-allyl-4-hydroxybenzoate → Methyl 4-hydroxy-3-propylbenzoate

HRID 363038Notes

Reaction equation

HRID 363038 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH2:12][CH:13]=[CH2:14]>CCOC(C)=O.[Pd]>[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH2:12][CH2:13][CH3:14]

Participants

4

Reactant 1

HCID 939882Methyl 3-allyl-4-hydroxybenzoate

Product 1

HCID 11805593Methyl 4-hydroxy-3-propylbenzoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To 22-3 (6.0 g, 33.2 mmol) in 50 mL of EtOAc was added 60 mg of 5% Pd on carbon and the whole was hydrogenated at atmospheric pressure for 24 h. Hydrogen was removed from the reaction mixture and the solution was filtered through Celite. Evaporation of the solvent afforded product 22-4 as a white solid.

Workup

  1. customHydrogen was removed from the reaction mixture
  2. filtrationthe solution was filtered through Celite
  3. customEvaporation of the solvent

Sources & evidence

ORD record
ord-f01451e0f3f640d8932c8f76d798ecf0
Source dataset
uspto-grants-1999_02
Patent number
US05872138

Reaction notes

Loading…