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

HRID 736126Notes

Reaction equation

HRID 736126 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>>[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

4

Reactant 3

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

Product 1

HCID 23291322-Chloro-5-(methylsulphonyl)benzoic acidYield 70%

Conditions

Temperature
0 °C

Procedure

A solution of 2-Chloro-5-(methylthio)benzoic acid (CAS: 51546-12-4; 2.5 g, 11.8 mmol) was dissolved in methanol (50 ml) and cooled to 0° C. Oxone (21.9 g, 35.5 mmol) was added portionwise within 5 minutes. The mixture was stirred at 0° C. for 30 minutes and then at room temperature for 22 hours. The mixture was filtered. The filtrate was poured onto water (200 ml). The aqueous layer was extracted with dichloromethane (5×50 ml). The combined extracts were dried over Na2SO4, filtered and the solvent was removed in vacuo. The solid was stirred in ether (30 ml), filtered and dried to provide the title compound (1.96 g, 70%) as a beige solid, MS (m/e): 232.9 (M−H+, 100%).

Workup

  1. waitat room temperature for 22 hours
  2. filtrationThe mixture was filtered
  3. additionThe filtrate was poured onto water (200 ml)
  4. extractionThe aqueous layer was extracted with dichloromethane (5×50 ml)
  5. dry with materialThe combined extracts were dried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent was removed in vacuo
  8. stirringThe solid was stirred in ether (30 ml)
  9. filtrationfiltered
  10. customdried

Sources & evidence

ORD record
ord-f416ca93172344198db7c7ac3ac6a8f2
Source dataset
uspto-grants-2009_09
Patent number
US07595314B2

Reaction notes

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