Dimethyl Sulfate → Oxirane, 2-methyl-2-[4-(2-methylpropyl)phenyl]-

Participants

Reaction Steps

24.8 g (0.2 mole) of thioanisole was heated to 90° C. with stirring, 27.8 g (0.22 mole) of dimethyl sulfate was added thereto at 90°-95° C. over a period of 30 minutes and stirred for another 30 minutes at the same temperature. To the reaction mixture, 100 ml of toluene was added portionwise so as to maintain the temperature above 80° C. and then the mixture was cooled gradually with stirring to afford a suspension of phenyldimethylsulfonium methylsulfate in quantititative yield. To the suspension, 26.4 g (0.15 mole) of p-isobutylacetophenone and 16.0 g (0.4 mole) of powdered sodium hydroxide was added and the mixture was stirred for 8 hours at 50° C. The reaction mixture was worked up in the same manner as described in Example 6 to afford 24.7 g of 2-(4-isobutylphenyl)-1,2-epoxypropane in 86.7% yield.

Provenance & Evidence