Phosphorus pentachloride → 3-(Chlorosulfonyl)propyl acetate

HRID 1447068Notes

Reaction equation

HRID 1447068 reaction equation
P(Cl)(Cl)(Cl)(Cl)[Cl:2].[Na+].[C:8]([O:11][CH2:12][CH2:13][CH2:14][S:15]([O-:18])(=O)=[O:16])(=[O:10])[CH3:9]>>[C:8]([O:11][CH2:12][CH2:13][CH2:14][S:15]([Cl:2])(=[O:18])=[O:16])(=[O:10])[CH3:9]

Participants

3

Reactant 2

HCID 24819Phosphorus pentachloride3×HCID 588713853-Acetyloxy-1-propanesulfonic acid sodium salt

Product 1

HCID 105842113-(Chlorosulfonyl)propyl acetate

Procedure

A 100 g (0.48 mol) portion of phosphorus pentachloride is added to a flask containing 82.0 g (0.4 mol) of the above sulfonic acid salt. When the initial reaction subsides, the mixture is heated on the steam bath for 1 hr and 25 g of phosphorus pentachloride is added. Heating is continued for another 2.5 hr and another 10 g of phosphorus pentachloride is added and heating continued for 30 min. The dark reaction mixture is cooled and filtered and the filtrate distilled. The clear distillate is redistilled to give 42.3 g of 3-acetyloxy-1-propanesulfonyl chloride; bp 69°-81°/0.03 mm.

Workup

  1. customWhen the initial reaction subsides
  2. temperaturethe mixture is heated on the steam bath for 1 hr
  3. temperatureHeating
  4. temperatureheating
  5. waitcontinued for 30 min
  6. customThe dark reaction mixture
  7. temperatureis cooled
  8. filtrationfiltered
  9. distillationthe filtrate distilled
  10. distillationThe clear distillate is redistilled

Sources & evidence

ORD record
ord-13b28df959814b23a31e83d86cb87049
Source dataset
uspto-grants-1982_02
Patent number
US04315014

Reaction notes

Loading…