Methanol → Methyl 3-(methylsulfonyl)benzoate

HRID 1814701Notes

Reaction equation

HRID 1814701 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=[O:9])(=[O:4])=[O:3].S(=O)(=O)(O)O.[CH3:19]O>>[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([O:10][CH3:19])=[O:9])(=[O:3])=[O:4]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 2203803-Methanesulfonylbenzoic acid

Product 1

HCID 6432252Methyl 3-(methylsulfonyl)benzoateYield 81%

Procedure

To a solution of 3-methylsulfonylbenzoic acid (10 g, 50 mmol) in anhydrous methanol (100 mL) was added conc. sulfuric acid (10 mL). The mixture was refluxed for 4 hours and then concentrated to one-third volume. Water (200 mL) was added, and the mixture was extracted with diethyl ether. The organic extract was washed with 10% sodium carbonate solution, and dried over Na2SO4. After concentration, 8.6 g (81%) of methyl 3-methylsulfonylbenzoate was obtained.

Workup

  1. temperatureThe mixture was refluxed for 4 hours
  2. concentrationconcentrated to one-third volume
  3. additionWater (200 mL) was added
  4. extractionthe mixture was extracted with diethyl ether
  5. extractionThe organic extract
  6. washwas washed with 10% sodium carbonate solution
  7. dry with materialdried over Na2SO4
  8. concentrationAfter concentration

Sources & evidence

ORD record
ord-d80d30557d814ef6905a8cff697db101
Source dataset
uspto-grants-2005_04
Patent number
US06875760B2

Reaction notes

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