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

HRID 1154148Notes

Reaction equation

HRID 1154148 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 methylenchloride was dissolved 4.5 g of 2,3,5-trimethylanisole, and after cooling at -5°~-10° C., a solution (400 ml) of 6.0 ml of chlorosulfonic acid in methylene chloride was added dropwise to the mixture. The reaction mixture was kept at room temperature and then poured into ice-5% aqueous NaHCO3. The methylene chloride layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off and the residue was crystallized from n-hexane and filtered.

Workup

  1. temperatureafter cooling at -5°~-10° C.
  2. customwas kept at room temperature
  3. washThe methylene chloride layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off
  6. customthe residue was crystallized from n-hexane
  7. filtrationfiltered

Sources & evidence

ORD record
ord-d3ead4adc2794510a0bb27b474514578
Source dataset
uspto-grants-1984_12
Patent number
US04487726

Reaction notes

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