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

HRID 2167429Notes

Reaction equation

HRID 2167429 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 in 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 with 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-9544c3becf6d4650beebd0fa4648a93b
Source dataset
uspto-grants-2015_06
Patent number
US09045465B1

Reaction notes

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