Reaction #43888

Reaction equation

potassium 4-ethoxycarbonylbenzenesulfonate

POCl3

→

white solid

4-Ethoxycarbonylbenzenesulfonyl Chloride

Solvents

acetonitrile

sulfolane

Conditions

Workup

1. 1
   OtherA round bottom flask, fitted with a magnetic stir bar and a hose adapter
2. 2
   Temperatureto cool to room temperature
3. 3
   Concentrationwas then concentrated
4. 4
   Othera rotary evaporator
5. 5
   TemperatureThe flask was then cooled in an ice bath
6. 6
   workup.ADDITIONice was added to the mixture in the flask
7. 7
   OtherThe product crystallized as a white solid
8. 8
   Filtrationwas filtered
9. 9
   Washwashed
10. 10
    OtherThe product was dried under vacuum at room temperature

Procedure

A round bottom flask, fitted with a magnetic stir bar and a hose adapter connected to a source of nitrogen gas, was charged with a solution of potassium 4-ethoxycarbonylbenzenesulfonate (75.1 g) dissolved in a 3:1 (v/v) mixture of acetonitrile (300 mL) and sulfolane (100 mL). As the solution was stirred, POCl3 (55 mL) was added slowly and the stirring mixture was heated at 75° C. under a nitrogen atmosphere for 3 hours. The heterogeneous reaction mixture was allowed to cool to room temperature and was then concentrated using a rotary evaporator. The flask was then cooled in an ice bath and ice was added to the mixture in the flask. The product crystallized as a white solid and was filtered and washed with cold deionized water. The product was dried under vacuum at room temperature and 3 mmHg for 2 hours to afford 76 g of white solid.

Source