Methanol → Methyl 3-(methylsulfonyl)benzoate

HRID 877434Notes

Reaction equation

HRID 877434 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].[CH3:14]O>>[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([O:10][CH3:14])=[O:9])(=[O:3])=[O:4]

Participants

3

Reactant 2

HCID 887MethanolHCID 2203803-Methanesulfonylbenzoic acid

Product 1

HCID 6432252Methyl 3-(methylsulfonyl)benzoateYield 99%

Procedure

To a stirred solution of 3-(methylsulfonyl)benzoic acid (1) (1.5 g, 7.5 mmol) in methanol (25 mL) sulfuric acid (1.5 mL) was added and the reaction mixture was heated to reflux for 8 h. On completion, solvent was removed, diluted with water (40 mL) and extracted with ethyl acetate (60 mL×3). The combined organic layer was washed saturated sodium bicarbonate solution, brine, dried over sodium sulphate and concentrated to afford the title compound 2 (1.6 g, 99%) which was used for further reaction.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 8 h
  3. customOn completion, solvent was removed
  4. additiondiluted with water (40 mL)
  5. extractionextracted with ethyl acetate (60 mL×3)
  6. washThe combined organic layer was washed saturated sodium bicarbonate solution, brine
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-6c859f4f169d4f2ba9aee4af674eb538
Source dataset
uspto-grants-2015_03
Patent number
US08987318B2

Reaction notes

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