3-Benzoylbenzoic acid → 3-Benzylbenzoic acid

HRID 411322Notes

Reaction equation

HRID 411322 reaction equation
[C:1]([C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12]([OH:14])=[O:13])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(OCC)(=O)C.OS(O)(=O)=O.CCCCCC.[Pd]>[CH2:1]([C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12]([OH:14])=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 1

HCID 1013863-Benzoylbenzoic acid

Product 1

HCID 41245533-Benzylbenzoic acid

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 1118Sulfuric AcidSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a Parr bottle containing 3-benzoylbenzoic acid (0.044 moles) (Aldrich) in 150 mL of ethyl acetate and 4.5 mL of concentrated H2SO4 was added 10 grams of 5% Pd/C. The mixture was hydrogenated on a Parr apparatus under hydrogen (45 psi) overnight. The reaction mixture was then filtered through Hyflo, washing with ethyl acetate. The filterate was dried over Na2SO4, filtered and concentrated to give an oil. The oil was slurried in hexane and the resulting white solid was collected by filtration to afford 3-benzylbenzoic acid, which was used without further purification.

Workup

  1. filtrationThe reaction mixture was then filtered through Hyflo
  2. washwashing with ethyl acetate
  3. dry with materialThe filterate was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give an oil
  7. filtrationthe resulting white solid was collected by filtration

Sources & evidence

ORD record
ord-288365347ce34155a599143c5461cfa3
Source dataset
uspto-grants-2003_05
Patent number
US06559141B2

Reaction notes

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