Reaktion #74931

Reaktionsgleichung

hydrogen sulfide

phosphorus pentasulfide

hydrogen sulfide

sodium hydroxide

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

→

2,3-diphenyl-5-p-tolylthiophene

Ausbeute 107.4%

Lösungsmittel

ethanol

xylene

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle