Chlorosulfonic acid → 4-Methoxy-2,3,5,6-tetramethylbenzenesulfonyl chloride

HRID 1154146Notes

Reaction equation

HRID 1154146 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH3:9])=[C:4]([CH3:10])[C:3]=1[O:11][CH3:12].[Cl:13][S:14](O)(=[O:16])=[O:15]>ClCCl>[CH3:12][O:11][C:3]1[C:4]([CH3:10])=[C:5]([CH3:9])[C:6]([S:14]([Cl:13])(=[O:16])=[O:15])=[C:7]([CH3:8])[C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 2786643-Methoxy-1,2,4,5-tetramethylbenzene

Product 1

HCID 159175204-Methoxy-2,3,5,6-tetramethylbenzenesulfonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In 600 ml of dichloromethane was dissolved 10.0 g of 2,3,5,6-tetramethylanisole, followed by addition of a solution (400 ml) of 12 ml of chlorosulfonic acid in dichloromethane at -5°~-10° C. The mixture was kept stirred for 2 hours and the reaction mixture was poured into ice-5% aqueous NaHCO3. The organic layer was washed with water and dried over magnesium sulfate. The solvent was distilled off and the residue was crystallized from n-hexane and filtered.

Workup

  1. washThe organic layer was washed with water
  2. dry with materialdried over magnesium sulfate
  3. distillationThe solvent was distilled off
  4. customthe residue was crystallized from n-hexane
  5. filtrationfiltered

Sources & evidence

ORD record
ord-c254c37c89bf40f29c916ef78cc2ef2d
Source dataset
uspto-grants-1984_12
Patent number
US04487726

Reaction notes

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