Benzene → 1-Phenyl-1,4-pentanedione

HRID 2357715Notes

Reaction equation

HRID 2357715 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[O:5]=[C:6]([CH3:12])[CH2:7][CH2:8][C:9](Cl)=[O:10].Cl.[CH:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[C:14]1([C:9](=[O:10])[CH2:8][CH2:7][C:6](=[O:5])[CH3:12])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 4

HCID 241BenzeneHCID 313Hydrochloric AcidHCID 6451240Aluminum(III) ChlorideHCID 123004064-Oxopentanoyl chloride

Product 1

HCID 1363711-Phenyl-1,4-pentanedioneYield 24.07%

Procedure

To a well stirred suspension of anhydrous aluminium chloride (27.0 g, 205.9 mmol) in 126 ml of benzene was added 4-oxopentanoylchloride (23.0 g, 171.6 mmol) drop-wise, over a period of 30-35 minutes at room temperature (25-30° C.). The reaction mixture was stirred at the same temperature for 1 hour. After decomposition of the reaction mixture by the addition of solid ice and hydrochloric acid (10 ml) the precipitated solid was filtered and the filtrate evaporated on a rotary evaporator to remove all the solvents. The residue was dissolved in ethyl acetate (400 ml), washed with water (2×100 ml), brine (100 ml) and dried over anhydrous sodium sulfate and the solvent evaporated off. The crude product so obtained was chromatographed over silica gel (100-200 mesh) using chloroform as eluent to give 8.6 g (24.07%) of the title compound.

Workup

  1. stirringThe reaction mixture was stirred at the same temperature for 1 hour
  2. filtrationwas filtered
  3. customthe filtrate evaporated on a rotary evaporator
  4. customto remove all the solvents
  5. dissolutionThe residue was dissolved in ethyl acetate (400 ml)
  6. washwashed with water (2×100 ml), brine (100 ml)
  7. dry with materialdried over anhydrous sodium sulfate
  8. customthe solvent evaporated off
  9. customThe crude product so obtained
  10. customwas chromatographed over silica gel (100-200 mesh)

Sources & evidence

ORD record
ord-5399b74dd3cb49d084096b1a4cc49829
Source dataset
uspto-grants-2010_07
Patent number
US07763602B2

Reaction notes

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