Toluene → Benzenesulfonyl chloride

HRID 1786712Notes

Reaction equation

HRID 1786712 reaction equation
[C:1]1([S:7]([O-:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na+].C1(S([O-])=O)C=CC=CC=1.C1(C)C=CC=CC=1.[Cl:27]Cl>O>[C:1]1([S:7]([Cl:27])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 24526ChlorineHCID 2723840Benzenesulfinic acid, sodium saltHCID 3857574Benzenesulfinate

Product 1

HCID 7369Benzenesulfonyl chlorideYield 133.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A reactor was charged with 29.3 g of sodium benzenesulfinate (0.14 mole) obtained by the fourth step, and the benzenesulfinate was dissolved in 65 mL of water. Then, 105 mL of toluene was charged, and 10.3 g (0.1456 mole, 1.04 times moles) of chlorine was, little by little, blown into the reactor at a temperature of 18 to 20° C. The reaction solution was aged at the same temperature of 18 to 20° C. with stirring, and separated into an organic layer and an aqueous layer. The organic layer was washed with 90 g of a 3% aqueous sodium chloride solution and then concentrated at a reduced pressure and 45° C. or less to obtain 32.9 g of a benzenesulfonyl chloride solution. Gas chromatographic quantitative analysis revealed that the concentration of benzenesulfonyl chloride in the organic layer was 70.7% (weight; 24.21 g, 0.1371 mole), and the yield was 93.9%

Workup

  1. customobtained by the fourth step
  2. customblown into the reactor at a temperature of 18 to 20° C
  3. customwas aged at the same temperature of 18 to 20° C.
  4. customseparated into an organic layer
  5. washThe organic layer was washed with 90 g of a 3% aqueous sodium chloride solution
  6. concentrationconcentrated at a reduced pressure and 45° C. or less

Sources & evidence

ORD record
ord-ad4a09b75ec84bed8558cde3ba78f108
Source dataset
uspto-grants-2009_03
Patent number
US07507812B2

Reaction notes

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