Dibenzoylmethane → 1,3-Diphenylpropane

HRID 1900621Notes

Reaction equation

HRID 1900621 reaction equation
[C:1]([CH2:9][C:10](=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>[Pd].C(OCC)(=O)C.S(=O)(=O)(O)O>[C:2]1([CH2:1][CH2:9][CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 8433DibenzoylmethaneHCID 178418361HCID 178418361, compound

Product 1

HCID 141251,3-DiphenylpropaneYield 86.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 1118Sulfuric AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of dibenzoylmethane (100 g) and 5% palladium on carbon (10.0 g) in ethyl acetate (600 ml) and concentrated sulfuric acid (15 ml) was hydrogenated at a hydrogen pressure of 60 psi and at room temperature. After 2 hours, the reaction was allowed to cool to room temperature. Reaction mixture filtered through talc. The filtrate was treated with water (2×250 ml) and phases separated. The organic phase was treated with saturated aqueous sodium bicarbonate (250 ml). The organic phase was dried over sodium chloride then magnesium sulfate, filtered, concentrated vacuo to give 75.34 g of 1,3-diphenylpropane.

Workup

  1. customReaction mixture
  2. filtrationfiltered through talc
  3. additionThe filtrate was treated with water (2×250 ml) and phases
  4. customseparated
  5. additionThe organic phase was treated with saturated aqueous sodium bicarbonate (250 ml)
  6. dry with materialThe organic phase was dried over sodium chloride
  7. filtrationmagnesium sulfate, filtered
  8. concentrationconcentrated vacuo

Sources & evidence

ORD record
ord-acf205590e87463c8ff09c22ae905484
Source dataset
uspto-grants-1996_11
Patent number
US05576323

Reaction notes

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