3-Chlorobenzylideneacetone → 4-(3-Chlorophenyl)butan-2-one

HRID 840996Notes

Reaction equation

HRID 840996 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10](=[O:12])[CH3:11])[CH:5]=[CH:6][CH:7]=1.[H][H]>C(O)C.[Pt]=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][C:10](=[O:12])[CH3:11])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 1415763-ChlorobenzylideneacetoneHCID 178418361HCID 178418361, compound

Product 1

HCID 2604324-(3-Chlorophenyl)butan-2-oneYield 54.8%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

1-(3-Chlorophenyl)-1-buten-3-one (20.0 g, 111 mmol) was subjected to hydrogen catalytic reduction in ethanol (200 ml) at room temperature by using platinum oxide (PtO2; 0.30 g) as a catalyst. The catalyst was filtered off and the resulting filtrate was concentrated under reduced pressure. The resulting residue was purified by a silica gel column chromatography to obtain 11.1 g of 1-(3-chlorophenyl)butan-3-one.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe resulting filtrate was concentrated under reduced pressure
  3. customThe resulting residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-87a6163a9cd54890a32d9ee6d8468af8
Source dataset
uspto-grants-2002_04
Patent number
US06369110B1

Reaction notes

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