Hydrochloric Acid → 1-(4-Chlorophenyl)pentane-1,4-dione

HRID 638796Notes

Reaction equation

HRID 638796 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[O:5]=[C:6]([CH3:12])[CH2:7][CH2:8][C:9](Cl)=[O:10].Cl.[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([C:9](=[O:10])[CH2:8][CH2:7][C:6](=[O:5])[CH3:12])=[CH:17][CH:16]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 7964ChlorobenzeneHCID 6451240Aluminum(III) ChlorideHCID 123004064-Oxopentanoyl chloride

Product 1

HCID 51687791-(4-Chlorophenyl)pentane-1,4-dioneYield 13.6%

Procedure

To a well stirred suspension of anhydrous aluminium chloride (29.66 g, 0.223 mol) in 154.7 ml of chlorobenzene was added 4-oxopentanoylchloride (25.0 g, 0.187 mol) 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 filtrate was concentrated in a rotary evaporation to remove all the solvents. The residue was dissolved in ethyl acetate (400 ml), washed with water (2×100 ml), brine (100 ml). The organic layer was 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-hexane (90:10) as eluent to give 5.3 g (13.60%) of the title compound.

Workup

  1. stirringThe reaction mixture was stirred at the same temperature for 1 hour
  2. filtrationwas filtered
  3. concentrationfiltrate was concentrated in a rotary evaporation
  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 materialThe organic layer was dried 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-f075465fca904029a45420978a34b366
Source dataset
uspto-grants-2010_04
Patent number
US07691837B2

Reaction notes

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