Toluene → 3-Methyl-indan-1-one

Participants

Reaction Conditions

Reaction Steps

As presented in the following reaction formula, a mixture of 3-phenylbutanoic acid (30 g, 0.18 mol) in thionyl chloride (SOCl2; 100 mL) was refluxed under heating for 2 hours, and then the thionyl chloride was removed. Toluene (200 mL) and aluminum chloride (AlCl3; 24 g, 0.18 mol) were added to the resulting mixture at 0° C., and the reaction mixture was stirred at 0° C. for 0.5 hours, followed by refluxing under heating. After the completion of reaction, the mixture was treated with ice water and then extracted twice with 200 mL of dichloromethane (DCM). The combined organic phase was washed with water (100 mL) and saturated brine (100 mL), and dried and concentrated with magnesium sulfate to give a crude product. The crude product was purified by gel column chromatography (using 100 g of silica gel (product of Merck Co., Ltd.)) using an eluent of pentane (PE):ethyl acetate (20:1 (by volume)) to give 3-methyl-2,3-dihydro-1H-inden-1-one (16 g, yield: 60%) as a brown oil.

Provenance & Evidence