Methanol → 2-Chloro-5-(methylsulphonyl)benzoic acid

HRID 1586174Notes

Reaction equation

HRID 1586174 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8](SC)=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].O[O:14][S:15]([O-:17])=O.[K+].[CH3:19]O>O>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([S:15]([CH3:19])(=[O:17])=[O:14])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 887MethanolHCID 6088142-Chloro-5-(methylsulfanyl)benzoic acidHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 23291322-Chloro-5-(methylsulphonyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 2-chloro-5-(methylthio)benzoic acid (25 g, 123 mmol) dissolved in methanol (500 ml) is cooled to 0°-5° C. and then OXONE™ (227.6 g, 370 mol) in water (500 ml) is added. The reaction mixture is stirred for 30 minutes at 0°-5° C. and then at room temperature for 4 hours. The reaction mixture is diluted with water, extracted with CHCl3 (3×200 ml) and the CHCl3 extracts are combined, washed with water, then brine and then are dried over MgSO4, filtered and evaporated to afford 5.13 g of 2-chloro-5-(methylsulfonyl)benzoic acid, m.p. 187°-188° C.

Workup

  1. temperatureis cooled to 0°-5° C.
  2. waitat room temperature for 4 hours
  3. extractionextracted with CHCl3 (3×200 ml)
  4. washwashed with water
  5. dry with materialbrine and then are dried over MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-0b54947c21464ff0bcfc1d794d923d0a
Source dataset
uspto-grants-1999_08
Patent number
US05942520

Reaction notes

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