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

HRID 985958Notes

Reaction equation

HRID 985958 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-

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

50 ml of chlorosulfonic acid were added within 30 minute dropwise to a solution of 13.7 g of p-nitrotoluene in 50 ml of chloroform under ice cooling. After the addition, the mixture was refluxed for 6 hours. After refluxing, the reaction mixture was poured into ice water and extracted with chloroform. The chloroform layer was washed with water and dehydrated. Evaporation of chloroform gave 15.5 g of 5-nitro-2-methyl-phenylsulfonyl chloride of the m.p. 43°-44° C.

Workup

  1. additionAfter the addition
  2. temperaturethe mixture was refluxed for 6 hours
  3. temperatureAfter refluxing
  4. extractionextracted with chloroform
  5. washThe chloroform layer was washed with water
  6. customEvaporation of chloroform

Sources & evidence

ORD record
ord-851312635953498290ca356122a6657f
Source dataset
uspto-grants-1987_12
Patent number
US04710509

Reaction notes

Loading…