Reacción #74931

Ecuación de reacción

hydrogen sulfide

phosphorus pentasulfide

hydrogen sulfide

sodium hydroxide

1,2-diphenyl-4-p-tolylbutane-1,4-dione

→

2,3-diphenyl-5-p-tolylthiophene

Rendimiento 107.4%

Disolventes

ethanol

xylene

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe autoclave was sealed
2. 2
   Temperaturachilled in a Dry Ice-acetone bath
3. 3
   TemperaturaThe autoclave was then heated at 160°-190° C. (920-1130 psig) for 225 minutes
4. 4
   OtroThe slurry thus formed
5. 5
   Filtraciónwas filtered
6. 6
   OtroThe residue was dried

Procedimiento

In a 1-liter stainless steel autoclave equipped with stirrer were placed 71 g (0.217 mole) of 1,2-diphenyl-4-p-tolylbutane-1,4-dione, 100 ml of xylene, and 45 g (0.101 mole) of phosphorus pentasulfide. The autoclave was sealed, chilled in a Dry Ice-acetone bath, and charged with 120 g (3.52 moles) of hydrogen sulfide. The autoclave was then heated at 160°-190° C. (920-1130 psig) for 225 minutes. The autoclave was cooled to room temperature and the hydrogen sulfide vented into an aqueous sodium hydroxide solution. The residue in the autoclave was stirred with 150 ml of absolute ethanol. The slurry thus formed was filtered. The residue was dried to give 35.4 g (50.0%) of crude 2,3-diphenyl-5-p-tolylthiophene, m.p. 110°-112° C. Recrystallization from 190 ml. of toluene and 625 ml. of ethanol gave 30.1 g (42.5%) of pure 2,3-diphenyl-5-p-tolylthiophene, m.p. 114°-116° C.

Fuente