Benzoic Acid → Benzoic acid, 3-(chlorosulfonyl)-

HRID 846303Notes

Reaction equation

HRID 846303 reaction equation
[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:10][S:11](O)(=[O:13])=[O:12].S(=O)(=O)(O)O.S(=O)(=O)(O)N.S(Cl)(Cl)=O>>[Cl:10][S:11]([C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=1)[C:1]([OH:9])=[O:8])(=[O:13])=[O:12]

Participants

6

Reactant 5

HCID 243Benzoic AcidHCID 1118Sulfuric AcidHCID 5987Sulfamic AcidHCID 24386Thionyl ChlorideHCID 24638Chlorosulfonic acid

Product 1

HCID 77641Benzoic acid, 3-(chlorosulfonyl)-

Conditions

Temperature
120 °C

Procedure

122.1 g (1.0 mol) of benzoic acid are introduced into a mixture of 349.5 g (3.0 mol) of chlorosulfonic acid, 20 g of 96% strength sulfuric acid and 1 g of sulfamic acid. The reaction mixture thus obtained is heated to 120° C. in the course of 3 hours and stirred until evolution of gas has ended. The mixture is then cooled to 70° C. and 119.0 g (1.0 mol) of thionyl chloride are added dropwise over the course of 2 hours. After it has been stirred at 80° C. for 30 minutes, the reaction mixture is added dropwise at 10° C. to ice water, and the precipitated crystals are filtered off with suction and washed with ice water. 232.1 g of 3-chlorosulfonylbenzoic acid (water content: 10%), corresponding to 208.9 g (94.7% of theory), calculated as dry material, having a melting point of 129°-131° C. are obtained.

Workup

  1. customThe reaction mixture thus obtained
  2. temperatureThe mixture is then cooled to 70° C.
  3. stirringAfter it has been stirred at 80° C. for 30 minutes
  4. filtrationthe precipitated crystals are filtered off with suction
  5. washwashed with ice water
  6. customare obtained

Sources & evidence

ORD record
ord-8f2ad886326946b68adbf15c7183f386
Source dataset
uspto-grants-1992_08
Patent number
US05136043

Reaction notes

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