4-Nitrotoluene → o-Toluenesulfonyl chloride, 5-nitro-

HRID 1038796Notes

Reaction equation

HRID 1038796 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[N+:6]([C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1)([O-:8])=[O:7]>C(Cl)(Cl)Cl>[N+:6]([C:9]1[CH:10]=[CH:11][C:12]([CH3:15])=[C:13]([S:2]([Cl:1])(=[O:5])=[O:3])[CH:14]=1)([O-:8])=[O:7]

Participants

4

Reactant 2

HCID 74734-NitrotolueneHCID 24638Chlorosulfonic acid

Product 1

HCID 8457o-Toluenesulfonyl chloride, 5-nitro-Yield 78.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Chlorosulfonic acid (50 mL, 750 mmol) was added within about 30 min dropwise to a solution of p-nitrotoluene (13.7 g, 100 mmol) in CHCl3 (50 mL) under ice cooling. After addition, the mixture was refluxed for about 6 h, cooled, the mixture poured into ice water (500 mL) and extracted with CHCl3 (3×300 mL). The CHCl3 layer was washed with water (2×200 mL) and dried with Na2SO4. Evaporation of CHCl3 gave 5-nitro-2-methyl-phenylsulfonyl chloride (18.4 g, 78%): 1H NMR (DMSO-d6) δ: 8.92 (d, J=2.4 Hz, 1H), 8.46 (dd, J=2.4 Hz, 1H), 7.66 (s, 1H), 2.92 (s, 3H).

Workup

  1. additionAfter addition
  2. temperaturethe mixture was refluxed for about 6 h
  3. temperaturecooled
  4. extractionextracted with CHCl3 (3×300 mL)
  5. washThe CHCl3 layer was washed with water (2×200 mL)
  6. dry with materialdried with Na2SO4
  7. customEvaporation of CHCl3

Sources & evidence

ORD record
ord-3b8bb0d6f9a34b9fbb4d1d499f7d6e3d
Source dataset
uspto-grants-2013_10
Patent number
US08551981B2

Reaction notes

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