Methanol → HCID 54190766, compound

HRID 266563Notes

Reaction equation

HRID 266563 reaction equation
[S:1]([O-:6])(O[O-])(=O)=[O:2].[K+].[K+].[CH3:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[C:12](SC)[CH:11]=1.[CH3:21]O>O>[CH3:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[C:12]([S:1]([CH3:21])(=[O:6])=[O:2])[CH:11]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 10313463Potassium peroxymonosulphateHCID 541520784-Methyl-2-(methylsulfanyl)benzoic acid

Product 1

HCID 54190766HCID 54190766, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of potassium peroxymonosulphate (23.8 g) in water was added to a solution of 4-methyl-2-methylsulphenylbenzoic acid (4.7 g) in methanol. The mixture was stirred for 5 hours and left to stand overnight at room temperature. The methanol was removed by evaporation and the resulting suspension was diluted with water and extracted with chloroform. The organic layer was dried (anhydrous magnesium sulphate) and filtered. The filtrate was evaporated to dryness and the residue was triturated with a mixture of ether and cyclohexane to give 4-methyl-2-methylsulphonylbenzoic acid (4.4 g) as a cream solid, m.p. 174°-174.5° C.

Workup

  1. waitleft
  2. waitto stand overnight at room temperature
  3. customThe methanol was removed by evaporation
  4. additionthe resulting suspension was diluted with water
  5. extractionextracted with chloroform
  6. dry with materialThe organic layer was dried (anhydrous magnesium sulphate)
  7. filtrationfiltered
  8. customThe filtrate was evaporated to dryness
  9. customthe residue was triturated with a mixture of ether and cyclohexane

Sources & evidence

ORD record
ord-a9d06d5515ab4750aebb99cd3f39608d
Source dataset
uspto-grants-1997_07
Patent number
US05650533

Reaction notes

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