Chloroform → Methyl cumenesulfonate

HRID 1744202Notes

Reaction equation

HRID 1744202 reaction equation
S(Cl)(Cl)=O.[C:5]1([CH:15]([CH3:17])[CH3:16])[C:6]([S:11]([O-:14])(=[O:13])=[O:12])=[CH:7][CH:8]=[CH:9][CH:10]=1.[Na+].[CH:19](Cl)(Cl)Cl>CN(C=O)C>[C:5]1([CH:15]([CH3:17])[CH3:16])[C:6]([S:11]([O:14][CH3:19])(=[O:13])=[O:12])=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 24386Thionyl ChlorideHCID 23665765Sodium Cumenesulfonate

Product 1

HCID 86595654Methyl cumenesulfonateYield 44%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

594.9 g (5.0 mol) of thionyl chloride were initially introduced together with 1 g of DMF, and 222.2 g (1.0 mol) of sodium cumenesulfonate were slowly added in portions starting at room temperature. The mixture was stirred at reflux for 16 hours and 250 ml of chloroform were added after cooling. Following filtration, excess thionyl chloride was stripped off together with the chloroform under reduced pressure. 250 ml of methanol were added, and a pH of 7.0 was established using 25% strength sodium hydroxide solution at 25° C. The mixture was then stirred out with dichloromethane, the organic phase was concentrated on a rotary evaporator, and the residue obtained was subjected to fractional distillation under reduced pressure. At 102° C. and 0.03 mbar, 96.9 g (0.44 mol) of methyl cumenesulfonate were isolated in the form of a clear liquid, corresponding to a yield of 44%.

Workup

  1. additionwere slowly added in portions
  2. customstarting at room temperature
  3. temperatureat reflux for 16 hours
  4. temperatureafter cooling
  5. filtrationfiltration, excess thionyl chloride
  6. addition250 ml of methanol were added
  7. customat 25° C
  8. stirringThe mixture was then stirred out with dichloromethane
  9. concentrationthe organic phase was concentrated on a rotary evaporator
  10. customthe residue obtained
  11. distillationwas subjected to fractional distillation under reduced pressure

Sources & evidence

ORD record
ord-f8c9f015086d4fa4a1d0da8ea16d7e16
Source dataset
uspto-grants-2006_03
Patent number
US07015185B2

Reaction notes

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