Methyl 3-benzyloxy-5-phenylbenzoate → Methyl 3-hydroxy-5-phenylbenzoate

HRID 399851Notes

Reaction equation

HRID 399851 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH:16]=[C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:18]=1)[C:12]([O:14][CH3:15])=[O:13])C1C=CC=CC=1>C(O)(=O)C.[Pd]>[OH:8][C:9]1[CH:10]=[C:11]([CH:16]=[C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:18]=1)[C:12]([O:14][CH3:15])=[O:13]

Participants

4

Reactant 1

HCID 18945315Methyl 3-benzyloxy-5-phenylbenzoate

Product 1

HCID 18945322Methyl 3-hydroxy-5-phenylbenzoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of methyl 3-benzyloxy-5-phenylbenzoate (10 g) in acetic acid (300 ml) was added 10% palladium on carbon (1 g), and the mixture was subjected to catalytic hydrogenation at 80° C. under atmospheric pressure. The catalyst was removed by filtration and the filtrate was evaporated in vacuo. To the residue were added ethyl acetate and water, and adjusted to pH 5 with potassium carbonate. The separated organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo to give methyl 3-hydroxy-5-phenylbenzoate.

Workup

  1. customwas subjected to catalytic hydrogenation at 80° C. under atmospheric pressure
  2. customThe catalyst was removed by filtration
  3. customthe filtrate was evaporated in vacuo
  4. additionTo the residue were added ethyl acetate and water
  5. washThe separated organic layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-c3fa27934c0e4a19b3b704796311bb8e
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Reaction notes

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