3-Phenylphthalide → o-Benzylbenzoic acid

HRID 46810

Reaction equation

HRID 46810 reaction equation
[C:1]1([CH:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:9](=[O:10])[O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>[Pd].C(O)C>[C:1]1([CH2:7][C:16]2[C:11]([C:9]([OH:10])=[O:8])=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 953653-Phenylphthalide

Product 1

HCID 11924o-Benzylbenzoic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 55.2 g. of 3-phenyl phthalide (0.263 mole), 600 ml. ethanol and 5.9 g. of 10% Pd/C is hydrogenated at room temperature and 50 psi until 1 equivalent of H2 is absorbed. The catalyst is removed by filtration and the solvent removed in vacuo and the residue triturated in petroleum ether to give α-phenyl-o-toluic acid; m.p. 101°-104° C.

Workup

  1. additionA mixture of 55.2 g
  2. customis hydrogenated at room temperature
  3. custom50 psi until 1 equivalent of H2 is absorbed
  4. customThe catalyst is removed by filtration
  5. customthe solvent removed in vacuo
  6. customthe residue triturated in petroleum ether

Sources & evidence

ORD record
ord-33535887a2214ee597df225001010316
Source dataset
uspto-grants-1979_11
Patent number
US04175191

Linked notes

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