Thionyl Chloride → 4-(3-Methylbutoxy)benzene-1-sulfonyl chloride

HRID 1531228Notes

Reaction equation

HRID 1531228 reaction equation
[CH3:1][CH:2]([CH3:16])[CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([O-])(=[O:14])=[O:13])=[CH:8][CH:7]=1.[Na+].S(Cl)([Cl:20])=O>CN(C)C=O>[CH3:1][CH:2]([CH3:16])[CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([Cl:20])(=[O:14])=[O:13])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 23701366Sodium 4-(3-methylbutoxy)benzenesulfonate

Product 1

HCID 183240014-(3-Methylbutoxy)benzene-1-sulfonyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

A mixture of sodium 4-(3-methylbutoxy)benzenesulfonate (2.5 grams, 9.4 mmole), thionyl chloride (10 mL), and 5 drops of N,N-dimethylformamide was heated at reflux for 5 hours. After cooling, the excess thionyl chloride was evaporated and the residue was taken up in ethyl acetate. The solution was cooled in an ice bath and water was added. The organic phase was separated and washed with water and brine. After drying over sodium sulfate, the solvent was evaporated to afford the title compound as an oil, 2.34 grams (95%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 5 hours
  3. temperatureAfter cooling
  4. customthe excess thionyl chloride was evaporated
  5. temperatureThe solution was cooled in an ice bath
  6. additionwater was added
  7. customThe organic phase was separated
  8. washwashed with water and brine
  9. dry with materialAfter drying over sodium sulfate
  10. customthe solvent was evaporated

Sources & evidence

ORD record
ord-4eced72fb9f14f47bad3401ec1b68b49
Source dataset
uspto-grants-2001_03
Patent number
US06197810B1

Reaction notes

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