Chlorosulfonic acid → 4-Methoxy-2,3,6-trimethylbenzenesulfonyl chloride

HRID 1632466Notes

Reaction equation

HRID 1632466 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH3:9])=[CH:4][C:3]=1[O:10][CH3:11].[Cl:12][S:13](O)(=[O:15])=[O:14]>C(Cl)Cl>[CH3:11][O:10][C:3]1[CH:4]=[C:5]([CH3:9])[C:6]([S:13]([Cl:12])(=[O:15])=[O:14])=[C:7]([CH3:8])[C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 885552,3,5-Trimethylanisole

Product 1

HCID 5627874-Methoxy-2,3,6-trimethylbenzenesulfonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In 500 ml of methylene chloride was dissolved 4.5 g of 2,3,5-trimethylanisole and the solution was cooled to -5° C. to -10° C. A solution of 6.0 ml of chlorosulfonic acid in 400 ml of methylene chloride was added dropwise, and then the temperature was allowed to rise to room temperature. The mixture was poured into an ice--5% aqueous sodium hydrogen carbonate mixture. The methylene chloride layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was then distilled off, and the residue was crystallized from n-hexane.

Workup

  1. temperaturethe solution was cooled to -5° C. to -10° C
  2. customto rise to room temperature
  3. washThe methylene chloride layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was then distilled off
  6. customthe residue was crystallized from n-hexane

Sources & evidence

ORD record
ord-1384fd2f7d624c3081fa671dcf5da80f
Source dataset
uspto-grants-1984_10
Patent number
US04476051

Reaction notes

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