Hydrochloric Acid → Benzenesulfonyl chloride

HRID 596930Notes

Reaction equation

HRID 596930 reaction equation
[C:1]1([S:7]([Cl:10])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[ClH:11].ClCl>[Fe]>[C:1]1([S:7]([Cl:10])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:11][C:3]1[CH:2]=[C:1]([S:7]([Cl:10])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 7369Benzenesulfonyl chlorideHCID 24526Chlorine

Product 2

HCID 7369Benzenesulfonyl chlorideYield 19%HCID 179093-Chlorobenzenesulphonyl chloride

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

706 g (4 mols) of benzene sulphonyl chloride and 10 g of iron filings are initially placed in a 2-liter stirrer-type apparatus. The mixture is saturated with gaseous hydrochloric acid and chlorine is introduced at 50° to 60° C until there is an increase in weight of 150 g. Distillation takes place after removal of the catalyst. 741 g of crude product of b.p.: 113° to 120° C/3 mm.Hg are obtained. By fine rectification, 133 g of benzene sulphonyl chloride (19% recovery) of b.p.: 89° C/1.3 mm.Hg and 572 g of m-chlorobenzene sulphonyl chloride (yield relative to reacted benzene sulphonyl chloride = 83% of the theoretical) of b.p.: 102° C/1.6 to 1.7 mm.Hg are obtained.

Workup

  1. additionis introduced at 50° to 60° C until there
  2. temperaturean increase in weight of 150 g
  3. distillationDistillation
  4. customafter removal of the catalyst
  5. custom741 g of crude product of b.p.: 113° to 120° C/3 mm.Hg are obtained

Sources & evidence

ORD record
ord-1066973ffb704b31aecf0153fff2ff07
Source dataset
uspto-grants-1977_03
Patent number
US04012442

Reaction notes

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