Methanesulfonic Acid → Benzene, 1-methoxy-4-(methylsulfonyl)-

HRID 2051046Notes

Reaction equation

HRID 2051046 reaction equation
[C:1]1([O:7][CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:9][S:10](O)(=[O:12])=[O:11].P(Cl)(Cl)(Cl)=O>>[CH3:8][O:7][C:1]1[CH:6]=[CH:5][C:4]([S:10]([CH3:9])(=[O:12])=[O:11])=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 6395Methanesulfonic AcidHCID 7519AnisoleHCID 24813Phosphorus oxychloride

Product 1

HCID 137966Benzene, 1-methoxy-4-(methylsulfonyl)-Yield 35%

Conditions

Temperature
122.5 °C

Procedure

Anisole (2.16.3 g, 2.0 moles) was mixed in a flask with anhydrous methane sulfonic acid (64.8 g, 1.0 mole) and phosphorus oxychloride (54.1 g, 0.56 mole) and was heated while stirring at 120-125° C. for 5 hours. A nitrogen purge was used to sweep out HCl gas as it formed. Subsequent treatment of the reaction mixture after cooling was the same as in Example 1. The washed and dried product solution was then heated in a distillation unit with a fractionating column to remove unreacted anisole. Products remaining in the distillation unit were finally diluted with N-butanol and crystallized from this solvent. A yield of 35% of methyl p-methoxyphenyl sulfone was obtained.

Workup

  1. temperaturewas heated
  2. customA nitrogen purge
  3. customformed
  4. temperatureSubsequent treatment of the reaction mixture after cooling
  5. washThe washed
  6. temperaturedried product solution was then heated in a distillation unit with a fractionating column
  7. customto remove unreacted anisole
  8. additionwere finally diluted with N-butanol
  9. customcrystallized from this solvent

Sources & evidence

ORD record
ord-b06e7081d4294405a85933d5b49efbb0
Source dataset
uspto-grants-1991_05
Patent number
US05015775

Reaction notes

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