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

HRID 377543Notes

Reaction equation

HRID 377543 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

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 at 5° C. 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 subsequently stirred for 1 hour at 5° C. and for 12 hours at room temperature. The pH was then brought to 1 using 10% strength hydrochloric acid, and 1500 ml of aqueous 40% strength sodium hydrogen sulfite solution were added. After the mixture had been stirred 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. After the solvent had been distilled off, 102.0 g of methyl 2-chloro-3-hydroxycarbonyl-4-methylsulfonylbenzoate were obtained.

Workup

  1. additionwere added
  2. stirringAfter the mixture had been stirred 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. distillationAfter the solvent had been distilled off

Sources & evidence

ORD record
ord-d9df11de04c349f3934a0c3b39541094
Source dataset
uspto-grants-2000_02
Patent number
US06028035

Reaction notes

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