Reaktion #74932

Reaktionsgleichung

hydrogen sulfide

phosphorus pentasulfide

hydrogen sulfide

sodium hydroxide

1,2-diphenyl4-p-chlorophenylbutane-1,4-dione

→

2,3-diphenyl-5-p-chlorophenylthiophene

Ausbeute 134.7%

Lösungsmittel

ethanol

xylene

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe autoclave was cooled with a Dry Ice-acetone bath
2. 2
   TemperaturThe autoclave was heated
3. 3
   TemperaturThe autoclave was cooled
4. 4
   FiltrationFiltration
5. 5
   Sonstigedrying
6. 6
   Sonstigegave a crude product of 61.2 g (80.2%) m.p. 115°-117°
7. 7
   SonstigeRecrystallization from 190 ml of toluene and 625 ml of ethanol

Vorschrift

In a 1-liter stainless steel autoclave equipped with stirrer were placed 76.9 g (0.220 mole) of 1,2-diphenyl4-p-chlorophenylbutane-1,4-dione, 100 ml of xylene and 45 g (0.101 mole) of phosphorus pentasulfide. The autoclave was cooled with a Dry Ice-acetone bath and charged with 120 g (3.52 moles) of hydrogen sulfide. The autoclave was heated with stirring for 200 minutes at 155°-178° C. (1000-2000 psig). The autoclave was cooled and the hydrogen sulfide allowed to escape into a sodium hydroxide solution. The residue was stirred with 150 ml of absolute ethanol. Filtration and drying gave a crude product of 61.2 g (80.2%) m.p. 115°-117°. Recrystallization from 190 ml of toluene and 625 ml of ethanol gave 47.2 g (61.9%) of pure 2,3-diphenyl-5-p-chlorophenylthiophene, m.p. 121°-122° C.

Quelle