Reaction #1442514

Reaction equation

thionylchloride

phenylmaleic anhydride

thionyl chloride

pyridine

→

3-Chloro-4-phenylfuran-2,5-dione

Solvents

toluene

Conditions

Workup

1. 1
   TemperatureWith ice-cooling
2. 2
   Temperatureheated at 75° C. for 10 min.
3. 3
   Temperatureto cool
4. 4
   Otherwas stripped off at 60° C. at reduced pressure
5. 5
   Filtrationfiltered
6. 6
   Washthe residue was washed with 50 ml of hot toluene
7. 7
   ConcentrationThe filtrate was concentrated under reduced pressure
8. 8
   Otherdried

Procedure

With ice-cooling, 10.0 g (57 mmol) of phenylmaleic anhydride were added to 57 ml of thionyl chloride, and the mixture was, over a period of 10 min, admixed dropwise with 9.08 g (115 mmol) of pyridine, the temperature being maintained at 10-12° C. The mixture was stirred at 10-12° C. for 30 min, heated at 75° C. for 10 min. using a preheated heating bath and allowed to cool, and excess thionylchloride was stripped off at 60° C. at reduced pressure. The residue was then boiled with 120 ml of toluene and filtered, and the residue was washed with 50 ml of hot toluene. The filtrate was concentrated under reduced pressure, titrated with petroleum ether and dried. Yield: 8.5 g, m.p. 82-83° C.

Source