Reacción #74934

Ecuación de reacción

hydrogen sulfide

phosphorus pentasulfide

hydrogen sulfide

sodium hydroxide

1,2-di-p-anisyl-4-p-chlorophenylbutane-1,4-dione

→

2,3-di-p-anisyl-5-p-chlorophenylthiophene

Rendimiento 153.3%

Disolventes

xylene

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe autoclave was cooled with a Dry Ice-acetone bath
2. 2
   Temperaturaheated for three hours at 162°-168° C. (1220-1290 psig)
3. 3
   OtroTreatment with 150 ml of absolute ethanol to remove unreacted phosphorus pentasulfide
4. 4
   Otrogave 77 g of crude product
5. 5
   OtroRecrystallization from 400 ml of absolute ethanol

Procedimiento

In a 1-liter stainless steel autoclave equipped with stirrer were placed 54.5 g (0.133 mole) of 1,2-di-p-anisyl-4-p-chlorophenylbutane-1,4-dione, 100 ml of xylene and 30 g (0.0675 mole) of phosphorus pentasulfide. The autoclave was cooled with a Dry Ice-acetone bath and 130 g (3.81 moles) of hydrogen sulfide was distilled into the autoclave. The vessel was stirred and heated for three hours at 162°-168° C. (1220-1290 psig). After cooling to room temperature the hydrogen sulfide was vented into an aqueous sodium hydroxide solution. Treatment with 150 ml of absolute ethanol to remove unreacted phosphorus pentasulfide gave 77 g of crude product. Recrystallization from 400 ml of absolute ethanol gave 45 g (83.1%) of pure 2,3-di-p-anisyl-5-p-chlorophenylthiophene, m.p. 125°-128° C.

Fuente