Water → p-Toluenesulfonic acid

HRID 1591388Notes

Reaction equation

HRID 1591388 reaction equation
O.[C:2]1([CH3:12])[CH:7]=[CH:6][C:5]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.O>C1C=CC=CC=1>[C:2]1([CH3:12])[CH:3]=[CH:4][C:5]([S:8]([OH:11])(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 962WaterHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 6101p-Toluenesulfonic acidYield 86.6%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Starting from 241.5 g of 4-toluenesulphonic acid hydrate, the water was eliminated using benzene. When water was no longer separated off, the benzene was distilled off. Any remaining benzene was expelled in a stream of nitrogen. 189.9 g (1.10 mol) of 4-toluenesulphonic acid were obtained. Then, chlorine was passed in at 60° C. until the increase in weight of the batch corresponded to the theoretically expected increase (39 g). After remaining chlorine and hydrogen chloride had been expelled in a stream of nitrogen, the effective increase in weight of the batch was 37.4 g (1.06 mol of chlorine). High-performance liquid chromatography analysis (HPLC) showed a content of 88.3% (88.3% of the theoretical yield) of 2-chloro-4-toluenesulphonic acid besides 1.72% (1.72% of the theoretical yield) of 3-chloro-4-toluenesulphonic acid and 1.3% (1.56% of the sulphonic acid employed) of 4-toluenesulphonic acid.

Workup

  1. customWhen water was no longer separated off
  2. distillationthe benzene was distilled off

Sources & evidence

ORD record
ord-63c7cd70d3224bec8e931f07aad44469
Source dataset
uspto-grants-1993_04
Patent number
US05206427

Reaction notes

Loading…