Phosphorus pentachloride → Styrene-4-sulfonyl chloride

HRID 2222047Notes

Reaction equation

HRID 2222047 reaction equation
P(Cl)(Cl)(Cl)(Cl)[Cl:2].[Na+].[CH2:8]=[CH:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([O-:19])(=O)=[O:17])=[CH:12][CH:11]=1>O>[CH2:8]=[CH:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([Cl:2])(=[O:19])=[O:17])=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 24819Phosphorus pentachloride2×HCID 3571582Sodium 4-styrenesulfonate

Product 1

HCID 9855777Styrene-4-sulfonyl chlorideYield 66.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

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.

Workup

  1. customOne neck was fitted with a mechanical stirrer, and a second neck
  2. customwas fitted with a plastic tube
  3. customto collect hydrochloric acid
  4. customproduced by the reaction
  5. additionAfter the addition
  6. temperaturecooling the contents again to 0° C
  7. customThe mixture was transferred to a separating funnel
  8. customAn oily organic layer was collected
  9. extractionthe remaining aqueous solution was extracted with dichloromethane
  10. dry with materialdried with anhydrous sodium sulfate
  11. filtrationThis solution was filtered through a small silica gel (100 g) column
  12. customThe filtrate was collected
  13. customdichloromethane was removed under vacuum

Sources & evidence

ORD record
ord-88fcd6f3d34047f6861665dfb89ff0ef
Source dataset
uspto-grants-2008_05
Patent number
US07371273B2

Reaction notes

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