Nitric Acid → 4-Methyl-3-nitrobenzenesulfonyl chloride

HRID 1012301Notes

Reaction equation

HRID 1012301 reaction equation
[N+:1]([O-:4])(O)=[O:2].S(=O)(=O)(O)O.[C:10]1([CH3:20])[CH:15]=[CH:14][C:13]([S:16]([Cl:19])(=[O:18])=[O:17])=[CH:12][CH:11]=1>>[CH3:20][C:10]1[CH:15]=[CH:14][C:13]([S:16]([Cl:19])(=[O:18])=[O:17])=[CH:12][C:11]=1[N+:1]([O-:4])=[O:2]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 73974-Toluenesulfonyl chloride

Product 1

HCID 5606384-Methyl-3-nitrobenzenesulfonyl chlorideYield 88%

Procedure

To a mixed solution of fuming nitric acid (3.5 ml) and conc. sulfuric acid (5.4 ml) was added p-toluenesulfonyl chloride (5.00 g, 26.2 mmol) in several portions under ice-cooling, and the mixture was stirred under ice-cooling for 2 hr. To the reaction mixture was added ice, and the mixture was extracted with diethyl ether. The organic layer was successively washed with water, saturated aqueous sodium hydrogen carbonate solution and saturated brine and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure to give 4-methyl-3-nitrobenzenesulfonyl chloride (5.43 g, yield 88.0%).

Workup

  1. temperaturecooling
  2. temperaturecooling for 2 hr
  3. additionTo the reaction mixture was added ice
  4. extractionthe mixture was extracted with diethyl ether
  5. washThe organic layer was successively washed with water, saturated aqueous sodium hydrogen carbonate solution and saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationAfter filtration
  8. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-fbc37182efb9453b81faaa6e4d9d4211
Source dataset
uspto-grants-2011_07
Patent number
US07977331B1

Reaction notes

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