Hydrochloric Acid → Methyl 2-chloro-3-hydroxycarbonyl-4-methylsulfonylbenzoate

HRID 1368817Notes

Reaction equation

HRID 1368817 reaction equation
O.P([O-])([O-])(O)=O.[Na+].[Na+].OO.Cl([O-])=O.[Na+].[Cl:15][C:16]1[C:25]([CH:26]=[O:27])=[C:24]([S:28]([CH3:31])(=[O:30])=[O:29])[CH:23]=[CH:22][C:17]=1[C:18]([O:20][CH3:21])=[O:19].Cl.S([O-])(O)=[O:34].[Na+]>O.C(#N)C>[Cl:15][C:16]1[C:25]([C:26]([OH:34])=[O:27])=[C:24]([S:28]([CH3:31])(=[O:30])=[O:29])[CH:23]=[CH:22][C:17]=1[C:18]([O:20][CH3:21])=[O:19]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 61488Phosphoric acid, disodium salt, hydrateHCID 18517410Methyl 2-chloro-3-formyl-4-methylsulfonylbenzoateHCID 23665763Sodium BisulfiteHCID 23668197Sodium Chlorite

Product 1

HCID 18517418Methyl 2-chloro-3-hydroxycarbonyl-4-methylsulfonylbenzoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
5 °C

Procedure

At 5° C., 13.8 g (0.11 mol) of sodium hydrogen phosphate monohydrate in 170 ml of water, 49.3 g (0.43 mol) of 30% strength hydrogen peroxide solution and 66.2 g (0.59 mol) of 80% strength aqueous sodium chlorite solution were added in succession to a solution of 115.3 g (0.42 mol) of methyl 2-chloro-3-formyl-4-methylsulfonylbenzoate and 2000 ml of acetonitrile. The reaction solution was then stirred for 1 hour at 5° C. and for 12 hours at room temperature. The pH was then adjusted to 1 using 10% strength hydrochloric acid, and 1500 ml of aqueous 40% strength sodium hydrogen sulfite solution were added. After stirring for 1 hour at room temperature, the aqueous phase was extracted three times with ethyl acetate. The combined organic phases were washed with sodium hydrogen sulfite solution and dried. Removal of the solvent by distillation gave 102.0 g of methyl 2-chloro-3-hydroxycarbonyl-4-methylsulfonylbenzoate.

Workup

  1. additionwere added
  2. stirringAfter stirring for 1 hour at room temperature
  3. extractionthe aqueous phase was extracted three times with ethyl acetate
  4. washThe combined organic phases were washed with sodium hydrogen sulfite solution
  5. customdried
  6. customRemoval of the solvent
  7. distillationby distillation

Sources & evidence

ORD record
ord-1eca6bb276074d4f993fbcae728a8d25
Source dataset
uspto-grants-2003_06
Patent number
US06576596B1

Reaction notes

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