Hydrochloric Acid → 4-Chloro-3-(chlorosulphonyl)benzoic acid

HRID 376903Notes

Reaction equation

HRID 376903 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[Cl:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=1.Cl>O>[Cl:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][C:8]=1[S:2]([Cl:1])(=[O:5])=[O:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 63184-Chlorobenzoic AcidHCID 24638Chlorosulfonic acid

Product 1

HCID 756134-Chloro-3-(chlorosulphonyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

28.05 kg (16 l) of chlorosulfonic acid are initially introduced and 4.4 kg of 4-chlorobenzoic acid were added in the course of 10 minutes with stirring (no heat effect). In the course of 90 minutes, the mixture was heated to 130-135° C., during which evolution of HCl was to be observed. The mixture was subsequently stirred for 3 hours at the stated temperature, and allowed to cool and to stand overnight. The reaction mixture was then allowed to run with stirring onto a mixture of 70 kg of ice and 30 kg of water, during which the temperature must not climb above 10° C. The product was filtered off with suction, washed with 40 kg of water and dried in vacuo at 40° C.

Workup

  1. stirringThe mixture was subsequently stirred for 3 hours at the stated temperature
  2. temperatureto cool
  3. customclimb above 10° C
  4. filtrationThe product was filtered off with suction
  5. washwashed with 40 kg of water
  6. customdried in vacuo at 40° C.

Sources & evidence

ORD record
ord-cf9417b569df4750a0f842de6adaa6f3
Source dataset
uspto-grants-2000_02
Patent number
US06022899

Reaction notes

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