Anisole → 4-Methoxybenzenesulfonyl chloride

HRID 482711Notes

Reaction equation

HRID 482711 reaction equation
[C:1]1([O:7][CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:9][S:10](O)(=[O:12])=[O:11]>C(Cl)Cl>[CH3:8][O:7][C:1]1[CH:6]=[CH:5][C:4]([S:10]([Cl:9])(=[O:12])=[O:11])=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 7519AnisoleHCID 24638Chlorosulfonic acid

Product 1

HCID 74014-Methoxybenzenesulfonyl chlorideYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

108 grams of anisole (1.0 mol) was added to 700 ml of CH2Cl2 in a one-liter round bottom flask and cooled to 0°-5° C. While using ice-bath cooling to maintain the temperature below 10° C., 280 grams of chlorosulfonic acid (1.5 mol) was added dropwise with magnetic stirring over a 4 hour period. The solution was then carefully poured over ice (1500 grams) and the organic layer collected. The solution was washed in the cold 10% NaHCO3, and the organic layer collected, then dried over MgSO4 and filtered. The solvent was removed in a rotary evaporator under aspirator vacuum and crude 4-methoxy- benzenesulfonylchloride (72% yield) was obtained as a red oil in a sufficient state of purity to permit its use without further purification.

Workup

  1. temperaturecooled to 0°-5° C
  2. temperaturecooling
  3. additionwas added dropwise
  4. customthe organic layer collected
  5. washThe solution was washed in the cold 10% NaHCO3
  6. customthe organic layer collected
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customThe solvent was removed in a rotary evaporator under aspirator vacuum

Sources & evidence

ORD record
ord-b1ac4fb82acd4e98a099e3364e01c7a9
Source dataset
uspto-grants-1986_03
Patent number
US04575541

Reaction notes

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