Benzene → 1-Phenyl-1,4-pentanedione

반응식

[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

참가 물질

반응물 4

HCID 241Benzene

HCID 313Hydrochloric Acid

HCID 6451240Aluminum(III) Chloride

HCID 123004064-Oxopentanoyl chloride

생성물 1

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

실험 절차

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.