Dimethyl Sulfoxide → Methylthiomethyl p-tolyl sulfone

HRID 1086108Notes

Reaction equation

HRID 1086108 reaction equation
[CH3:1][S:2]([CH3:4])=O.C(OC(=O)C)(=O)C.C([O-])(=O)C.[Na+].[C:17]1([CH3:26])[CH:22]=[CH:21][C:20]([S:23]([O-:25])=[O:24])=[CH:19][CH:18]=1.[Na+]>[Cl-].[Na+].O.C(O)(=O)C>[CH3:1][S:2][CH2:4][S:23]([C:20]1[CH:21]=[CH:22][C:17]([CH3:26])=[CH:18][CH:19]=1)(=[O:25])=[O:24]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 2723791Sodium p-toluenesulfinate

Product 1

HCID 548421Methylthiomethyl p-tolyl sulfoneYield 34%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Dimethylsulfoxide (9.25 g, 118 mmol) and acetic anhydride (15.6 g, 153 mmol) were heated to 80° C. for 24 hours. The reaction solution was cooled to room temperature, then glacial acetic acid (90 ml), sodium acetate (9.7 g, 118 mmol) and sodium p-toluenesulfinate (31.6 g, 178 mmol, dried in vacuo overnight with P2O5 at 50° C.) were added. The mixture was heated to 100° C. for 24 hours. Brine (150 ml) was added and the solution was extracted with methylene chloride (5X, 100 ml). The organic extracts were washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo to give a gummy solid. The solid was recrystallized from 95% ethanol (3B) to yield 8.68 g of white crystals of (methylthio)(p-toluenesulfonyl)methane: m.p. 81°-83° C.

Workup

  1. temperatureThe mixture was heated to 100° C. for 24 hours
  2. extractionthe solution was extracted with methylene chloride (5X, 100 ml)
  3. washThe organic extracts were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a gummy solid
  8. customThe solid was recrystallized from 95% ethanol (3B)

Sources & evidence

ORD record
ord-eaabfa6b5c2d44e48310a6ef70333eff
Source dataset
uspto-grants-1991_04
Patent number
US05011938

Reaction notes

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