4-Benzyloxy-2-methoxybenzoic acid methyl ester → Methyl 4-hydroxy-2-methoxybenzoate

HRID 1377727Notes

Reaction equation

HRID 1377727 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]([O:13]CC2C=CC=CC=2)[CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]>CCOC(C)=O.[Pd]>[CH3:1][O:2][C:3]1[CH:12]=[C:11]([OH:13])[CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]

Participants

4

Reactant 1

HCID 108260394-Benzyloxy-2-methoxybenzoic acid methyl ester

Product 1

HCID 12532676Methyl 4-hydroxy-2-methoxybenzoateYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 2-methoxy-4-benzyloxybenzoate (40 g, 147 mmol) from Step 2 above in EtOAc (200 mL) in a Parr shaker flask was added 2 gm of 10% Pd/C catalyst. The reaction was shaken under on a Parr hydrogenation apparatus under 55 psi of H2 for 24 hours. The catalyst was filtered off under a blanket of argon and the solvent was removed under reduced pressure. The resulting solid washed with a small volume of EtOAc and filtered and dried in vacuo for 24 hours to give methyl 2-methoxy-4-hydroxybenzoate in 99% yield.

Workup

  1. filtrationThe catalyst was filtered off under a blanket of argon
  2. customthe solvent was removed under reduced pressure
  3. washThe resulting solid washed with a small volume of EtOAc
  4. filtrationfiltered
  5. customdried in vacuo for 24 hours

Sources & evidence

ORD record
ord-8cc783ae03d14379a6480bf852eefc83
Source dataset
uspto-grants-1997_09
Patent number
US05665719

Reaction notes

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