P-Xylene → HCID 12097434, compound

HRID 434144Notes

Reaction equation

HRID 434144 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.[Cl:9][S:10]([OH:13])(=O)=[O:11]>>[CH3:1][C:2]1[C:7]([S:10]([Cl:9])(=[O:13])=[O:11])=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[S:10]([Cl:9])(=[O:13])=[O:11]

Participants

3

Reactant 2

HCID 7809P-XyleneHCID 24638Chlorosulfonic acid

Product 1

HCID 12097434HCID 12097434, compound

Procedure

1,4-Dimethylbenzene (10.6 g, 0.1 mol) was added dropwise to chlorosulfonic acid (60 g, 0.51 mol ) at room temperature with stirring. After the addition was complete, the reaction mixture was heated to ˜100C for 1 hr, cooled to room temperature and poured onto ice-water-1,2-dichloromethane mixture with stirring. The organic layer was separated, washed with water (2×), dried over anhydrous MgSO4 and the solvent evaporated to give 2,5-dimethyl-1,3-benzenedisulfonyl chloride, 26 g (86%) as a viscous liquid that solidified on standing, mp 24-27° C. Reported 25-27C. (C. M. Suter, Organic Chemistry of Sulfur Compounds, Chapter 3).

Workup

  1. additionAfter the addition
  2. temperaturethe reaction mixture was heated to ˜100C for 1 hr
  3. additionpoured onto ice-water-1,2-dichloromethane mixture
  4. stirringwith stirring
  5. customThe organic layer was separated
  6. washwashed with water (2×)
  7. dry with materialdried over anhydrous MgSO4
  8. customthe solvent evaporated

Sources & evidence

ORD record
ord-765afe0dc3e84138afad5042e963da65
Source dataset
uspto-grants-2003_12
Patent number
US06670474B2

Reaction notes

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