Phosphorus pentachloride → Styrene-4-sulfonyl chloride

Participants

Reaction Conditions

Reaction Steps

About 320 g of phosphorus pentachloride was taken in a three-neck round-bottomed flask. One neck was fitted with a mechanical stirrer, and a second neck was fitted with a plastic tube to collect hydrochloric acid produced by the reaction. About 190 g of p-styrenesulfonate sodium salt was added in small portions to the phosphorus pentachloride through the third neck while cooling the flask to 0° C. After the addition, the contents were allowed to stir at ambient temperature for 2 hours. Deionized ice water was then added dropwise to the flask, cooling the contents again to 0° C. The mixture was transferred to a separating funnel using additional water. An oily organic layer was collected and the remaining aqueous solution was extracted with dichloromethane. The organic layer was then combined and dried with anhydrous sodium sulfate. This solution was filtered through a small silica gel (100 g) column. The filtrate was collected and dichloromethane was removed under vacuum to obtain 125 g of p-styrenesulfonyl chloride blocked acid monomer.

Provenance & Evidence