Pyridine → 1-(2-Chlorophenyl)propane-1,2-dione

HRID 216836Notes

Reaction equation

HRID 216836 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9](=[O:11])[CH3:10].[Cr](Cl)([O-])(=O)=[O:13].[NH+]1C=CC=CC=1.N1C=CC=CC=1>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:13])[C:9](=[O:11])[CH3:10]

Participants

5

Reactant 3

HCID 1049PyridineHCID 2293551-(2-Chlorophenyl)propan-2-oneHCID 178418287HCID 178418287, compound

Product 1

HCID 178656181-(2-Chlorophenyl)propane-1,2-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-chlorophenylacetone (10.800 g, 64.049 mmol) in 279 mL of CH2Cl2, pyridinium chlorochromate (41.418 g, 192.15 mmol), and pyridine (16 mL) in three portions were added over 2.5 hours and the mixture was refluxed under vigorous stirring. After 22 h, the mixture was removed from heat. The mixture was concentrated in vacuo to give a dark red syrup. The crude mixture was purified by column chromatography on a 120 g of Redi-Sep™ column using 0-10% gradient of EtOAc in hexane over 28 min as eluent to give 1-(2-chlorophenyl)propane-1,2-dione as yellow liquid: 1H NMR (400 MHz, choroform-d) δ ppm 7.66 (1H, dd, J=7.6, 1.8 Hz), 7.49-7.54 (1H, m), 7.38-7.45 (2H, m), 2.58 (3H, s); LC-MS: m/z 182.9 [N+H]+.

Workup

  1. temperaturethe mixture was refluxed under vigorous stirring
  2. customthe mixture was removed
  3. temperaturefrom heat
  4. concentrationThe mixture was concentrated in vacuo
  5. customto give a dark red syrup
  6. customThe crude mixture was purified by column chromatography on a 120 g of Redi-Sep™ column
  7. customover 28 min

Sources & evidence

ORD record
ord-3fed81546363448fabf6b9e24c6092bc
Source dataset
uspto-grants-2012_06
Patent number
US08193199B2

Reaction notes

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