Dibenzylidene acetone → 1,5-Diphenylpentan-3-one

HRID 1779276Notes

Reaction equation

HRID 1779276 reaction equation
[C:1]1([CH:7]=[CH:8][C:9](=[O:18])[CH:10]=[CH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>O1CCCC1.[Pd]>[C:12]1([CH2:11][CH2:10][C:9](=[O:18])[CH2:8][CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 1

HCID 95417Dibenzylidene acetone

Product 1

HCID 214961,5-Diphenylpentan-3-oneYield 49.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1,5-diphenyl-1,4-pentadien-3-one (50.9 g, 0.217 mole) in dry tetrahydrofuran (350 ml) was hydrogenated over 5% palladium on carbon (5.6 g) at room temperature under an atmosphere of hydrogen. After reduction, catalyst was filtered off, the filtrate was concentrated and the residue was distilled under reduced pressure to give 25.5 g of the title compound as a pale yellow oil having a boiling point of 160°-162° C./0.4 mmHg.

Workup

  1. filtrationAfter reduction, catalyst was filtered off
  2. concentrationthe filtrate was concentrated
  3. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-0b66eaa507714a7ebdeb7dec5db859e3
Source dataset
uspto-grants-1997_05
Patent number
US05627006

Reaction notes

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