反応 #74931

反応方程式

hydrogen sulfide

phosphorus pentasulfide

hydrogen sulfide

sodium hydroxide

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

→

2,3-diphenyl-5-p-tolylthiophene

収率 107.4%

溶媒

ethanol

xylene

反応条件

後処理

1. 1
   その他The autoclave was sealed
2. 2
   温度chilled in a Dry Ice-acetone bath
3. 3
   温度The autoclave was then heated at 160°-190° C. (920-1130 psig) for 225 minutes
4. 4
   その他The slurry thus formed
5. 5
   ろ過was filtered
6. 6
   その他The residue was dried

実験手順

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.

出典