Thionyl Chloride → 2-Methoxy-4-methylbenzene-1-sulfonyl chloride

HRID 322096Notes

Reaction equation

HRID 322096 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][O:6][C:7]1[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][C:8]=1[S:14]([OH:17])(=O)=[O:15]>CCCCCC>[CH3:5][O:6][C:7]1[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][C:8]=1[S:14]([Cl:3])(=[O:17])=[O:15]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 13012786HCID 13012786, compound

Product 1

HCID 113450482-Methoxy-4-methylbenzene-1-sulfonyl chlorideYield 59%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Thionyl chloride (350 ml, 2.5 ml/g) was cautiously added to 2-methoxy-4-methylbenzenesulfonic acid (from (b), 140 g, 0.587 moles) over a period of 30 minutes. The mixture was stirred and heated to reflux for 1 hour and at room temperature for 16 hours. The excess thionyl chloride was removed by evaporation under reduced pressure and the residue was partitioned between deionised water (300 ml) and dichloromethane (400 ml). The phases were separated and the organic phase dried (MgSO4), filtered and concentrated to give the crude product (70 g, 54% yield). The crude product was partially dissolved in hexane (490 ml) at reflux, hot filtered to remove insoluble material and allowed to cool. The precipitated product was collected to give the title compound (41.3 g, 59% recovery) as a white crystalline solid (m.p.=81-84° C.).

Workup

  1. temperatureheated
  2. customThe excess thionyl chloride was removed by evaporation under reduced pressure
  3. customthe residue was partitioned between deionised water (300 ml) and dichloromethane (400 ml)
  4. customThe phases were separated
  5. dry with materialthe organic phase dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give the crude product (70 g, 54% yield)
  9. temperatureat reflux
  10. filtrationhot filtered
  11. customto remove insoluble material
  12. temperatureto cool
  13. customThe precipitated product was collected

Sources & evidence

ORD record
ord-946832100600479d96d2c3e9f354afa3
Source dataset
uspto-grants-2001_04
Patent number
US06211223B1

Reaction notes

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