Thionyl Chloride → 4-Acetylbenzenesulfonyl chloride

HRID 866969Notes

Reaction equation

HRID 866969 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. Th 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. customTh residual sulfonyl chloride is crystallized from benzene/hexane

Sources & evidence

ORD record
ord-9f102b3d37824ffc85a7228d6916c444
Source dataset
uspto-grants-1978_07
Patent number
US04101661

Reaction notes

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