Dibenzoylmethane → 1,3-Diphenylpropane

HRID 1456624Notes

Reaction equation

HRID 1456624 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 in 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 in vacuo

Sources & evidence

ORD record
ord-cef2383ff8e844b3b6cf46e6cd41d566
Source dataset
uspto-grants-1998_12
Patent number
US05843997

Reaction notes

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