4-Benzoylbenzoic acid → 4-Benzylbenzoic acid

HRID 1358829Notes

Reaction equation

HRID 1358829 reaction equation
[C:1]([C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Pd].C(O)C.Cl(O)(=O)(=O)=O>[CH2:1]([C:9]1[CH:10]=[CH:11][C:12]([C:13]([OH:15])=[O:14])=[CH:16][CH:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 1

HCID 691474-Benzoylbenzoic acid

Product 1

HCID 1364294-Benzylbenzoic acidYield 101.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 24247Perchloric AcidSolvent

Procedure

10% Palladium on carbon (0.5 g) was added to a solution of 4-benzoyl-benzoic acid (11.31 g, 50 mmol) in ethanol (250 mL) and 70% perchloric acid (10 mL). The suspension was hydrogenated under 40 psi at room temperature for 8 hours. The catalyst was removed by filtration and the filtrate made neutral with aqueous sodium bicarbonate. Solvents were evaporated, and the residue was partitioned into ethyl acetate and dilute aqueous potassium hydroxide. The aqueous phase was acidified with hydrochloric acid. The precipitated acid was filtered, washed, and dried to give 4-benzyl-benzoic acid (10.74 g, ˜100%).

Workup

  1. customThe catalyst was removed by filtration
  2. customSolvents were evaporated
  3. customthe residue was partitioned into ethyl acetate and dilute aqueous potassium hydroxide
  4. filtrationThe precipitated acid was filtered
  5. washwashed
  6. customdried

Sources & evidence

ORD record
ord-34d27050f64e49a38749061ea4754351
Source dataset
uspto-grants-2003_07
Patent number
US06596876B2

Reaction notes

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