Reacción #514076

Ecuación de reacción

bis-(2-chloroethylsulfonyl)methane

3,5-dinitrobenzoic acid

triethylamine

3,5-dinitrobenzoic acid

→

bis(vinylsulfonyl)methane

Rendimiento 75.0%

Disolventes

acetone

acetone

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathen cooled to -30° C.
2. 2
   Filtraciónfiltered
3. 3
   Otroto remove triethylamine hydrochloride
4. 4
   OtroThe filtrate was evaporated to dryness on a rotary evaporator at 40° C.
5. 5
   OtroThe residue was recrystallized from methanol containing 0.3 percent (wt/vol) of 3,5-dinitrobenzoic acid

Procedimiento

To a well stirred solution of 53.84 g of bis-(2-chloroethylsulfonyl)methane in 300 ml of acetone containing 0.9 g of 3,5-dinitrobenzoic acid, was added dropwise at 20°-25° C. a solution of 40.48 g of triethylamine in 50 ml of acetone containing 0.15 g of 3,5-dinitrobenzoic acid. The reaction was stirred for 1 hour at 25° C. then cooled to -30° C. and filtered to remove triethylamine hydrochloride. The filtrate was evaporated to dryness on a rotary evaporator at 40° C. and water aspirator pressure. The residue was recrystallized from methanol containing 0.3 percent (wt/vol) of 3,5-dinitrobenzoic acid, to give 29.3 g (75 percent) of colorless crystalline bis(vinylsulfonyl)methane of m.p. 59°-61° C. This material readily dissolved in water to give a 2 percent by weight solution with no insoluble material present.

Fuente