Dimethyl Sulfone → Methyl 3-phenylpropionate

Participants

Reaction Steps

To a solution of dimethylsulfone (42 g, 0.45 mole) in dimethylsulfoxide (225 ml), 60% sodium hydride (17.9 g, 0.45 mole) was added in a small portion at 18°-20° C., stirring was continued at 65°-70° C. for 30 minutes, and then diluted with tetrahydrofuran (225 ml). Then to this mixture, a solution of methyl 3-phenylpropionate (36.6 g, 0.22 mole) obtained in above (1) in tetrahydro-furan (110 ml) was added dropwise at 33°-41° C., and reacted with stirring for 1 hour. After cooling, the reaction mixture was poured into diluted hydrochloric acid, and extracted 5 times with chloroform (100 ml). The organic layer was washed thrice with H2O (200 ml), saturated aqueous sodium bicarbonate (200 ml), then H2O (200 ml), dried over anhydrous MgSO4 and evaporated. The crude solid (60.8 g) was recrystallized from ethyl acetate to afford 24.7 g of 1-methylsulfonyl-4-phenylbutan-2-one as white needles having a melting point of 97.6-°98.4° C.

Provenance & Evidence