Thionyl Chloride → 4-Acetylbenzenesulfonyl chloride

HRID 2164144Notes

Reaction equation

HRID 2164144 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([O-:13])(=O)=[O:11])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[Na+].S(Cl)([Cl:17])=O>CN(C)C=O>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([Cl:17])(=[O:13])=[O:11])=[CH:6][CH:5]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 23668814Sodium 4-acetylbenzenesulphonate

Product 1

HCID 2664184-Acetylbenzenesulfonyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 100 g. of sodium 4-acetylbenzenesulfonate in 225 ml. of dimethylformamide is treated with 31 ml. of thionyl chloride and the mixture is stirred at room temperature for 5 minutes, then poured into 1 l. of ice water. The resulting precipitate of 4-acetylbenzenesulfonyl chloride is collected by filtration and washed with ice water. The still-damp product may be used as such without further purification. However, if purification is desired, the following procedure may be used: The product is dissolved in methylene chloride and the solution is dried and evaporated at reduced pressure. The residual sulfonyl chloride is crystallized from benzene/hexane; m.p. 83°-85° C.

Workup

  1. additionA suspension of 100 g
  2. additionpoured into 1 l
  3. filtrationThe resulting precipitate of 4-acetylbenzenesulfonyl chloride is collected by filtration
  4. washwashed with ice water
  5. customsuch without further purification
  6. customHowever, if purification
  7. dissolutionThe product is dissolved in methylene chloride
  8. customthe solution is dried
  9. customevaporated at reduced pressure
  10. customThe residual sulfonyl chloride is crystallized from benzene/hexane

Sources & evidence

ORD record
ord-38ebf99c53be421d87e3f78f71a842a0
Source dataset
uspto-grants-1979_01
Patent number
US04137408

Reaction notes

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