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

HRID 2288115Notes

Reaction equation

HRID 2288115 reaction equation
[CH:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([O-:18])(=O)=[O:16])=[CH:11][CH:10]=2)[CH2:5]CC[CH2:2]1.[Na+].S(Cl)([Cl:22])=O>CN(C)C=O>[CH3:2][CH:1]([CH3:5])[CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([Cl:22])(=[O:18])=[O:16])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 23697515Sodium 4-(2-cyclopentylethoxy)benzenesulfonate

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

A mixture of sodium 4-(2-cyclopentylethoxy)benzenesulfonate (2.5 grams, 8.6 mmole), thionyl chloride (15 mL), and a few 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, 2.24 grams (90%).

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-c09234b746fe467ea5e5aa2022ffd946
Source dataset
uspto-grants-2000_07
Patent number
US06087392

Reaction notes

Loading…