1-(p-Chlorophenyl)acetone → 3-(4-Chloro-phenyl)-but-3-en-2-one

HRID 597896Notes

Reaction equation

HRID 597896 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=1.[CH3:12][N+](C)=C.[I-]>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[CH2:12])[C:9](=[O:11])[CH3:10])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 796991-(p-Chlorophenyl)acetoneHCID 2724133Dimethyl(methylene)ammounium iodide

Product 1

HCID 589524173-(4-Chloro-phenyl)-but-3-en-2-oneYield 43%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
125 °C

Procedure

1-(4-Chloro-phenyl)-propan-2-one (8.6 g, 51 mmol) and Eschenmoser's salt (12.3 g, 66.3 mmol) were dissolved in glacial acetic acid and heated in a closed pressure tube at 125° C. under nitrogen for 1 h. After cooling to room temperature, the solution was concentrated. The residue was dissolved in EtOAc, washed with saturated NaHCO3 aqueous solution, dried (MgSO4), concentrated, and chromatographed (SiO2, 39:1-19:1 hexane/EtOAc) to give 3-(4-chloro-phenyl)-but-3-en-2-one as yellow oil (3.92 g, 43%).

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe solution was concentrated
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with saturated NaHCO3 aqueous solution
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customchromatographed (SiO2, 39:1-19:1 hexane/EtOAc)

Sources & evidence

ORD record
ord-ee5067cbbffb42dea6fe681942b0d23f
Source dataset
uspto-grants-2011_03
Patent number
US07897601B2

Reaction notes

Loading…