Dimethyl Sulfone → 1-[3,5-Bis(dimethylamino)-4-methylphenyl]-2-(methanesulfonyl)ethan-1-one

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Reaction Steps

A suspension of 18.8 g. of dimethylsulfone and 3.6 g. of sodium hydride (50% dispersion in oil) in 80 ml. of dimethylsulfoxide was stirred with the exclusion of moisture for 2 hours at 50° C. Thereupon, 23.6 g. of methyl 3,5-bis(dimethylamino)-4-methylbenzoate were added and the mixture was stirred at room temperature for 1.5 hours. The solution was diluted with 400 ml. of water and extracted twice with ethyl acetate. The ethyl acetate phases were combined, washed with water, dried over sodium sulfate and evaporated to dryness in vacuo. After recrystallization of the residue from methanol, there was obtained 3',5' -bis(dimethylamino)-4'-methyl-2-methylsulfonylacetophenone, having a melting point of 161°-163° C.

Provenance & Evidence