Hydrochloric Acid → 4-Acetylbenzenesulfonyl chloride

HRID 342649Notes

Reaction equation

HRID 342649 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.N([O-])=O.[Na+].[S:15](=[O:17])=[O:16].[ClH:18]>O.C(O)(=O)C>[C:8]([C:5]1[CH:6]=[CH:7][C:2]([S:15]([Cl:18])(=[O:17])=[O:16])=[CH:3][CH:4]=1)(=[O:10])[CH3:9]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1119Sulfur DioxideHCID 7468p-AminoacetophenoneHCID 23668193Sodium Nitrite

Product 1

HCID 2664184-Acetylbenzenesulfonyl chloride

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

100 g of para-amino acetophenone are dissolved in 124 ml of concentrated hydrochloric acid and the mixture is cooled to 0° C. A solution of 55.2 g of sodium nitrite in 90 ml of water are then added in keeping the temperature at 0° C. After 1 h of stirring, the solution obtained is added dropwise to a solution of 23 g of cupric chloride in 600 ml of glacial acetic acid saturated with sulphur dioxide. After stirring for 1 h at ambient temperature, the reaction mixture is poured into 2 l of ice-water mixture, then filtered off. The orange solid obtained is washed with water, then with pentane.

Workup

  1. customat 0° C
  2. customthe solution obtained
  3. stirringAfter stirring for 1 h at ambient temperature
  4. filtrationfiltered off
  5. customThe orange solid obtained
  6. washis washed with water

Sources & evidence

ORD record
ord-45d88ab0a62a49c2a90850801071bbcc
Source dataset
uspto-grants-1999_01
Patent number
US05859036

Reaction notes

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