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

HRID 1276119Notes

Reaction equation

HRID 1276119 reaction equation
O.P([O-])([O-])(O)=O.[Na+].[Na+].OO.[Cl-].[Na+].[Cl:13][C:14]1[C:23]([CH:24]=[O:25])=[C:22]([S:26]([CH3:29])(=[O:28])=[O:27])[CH:21]=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17].Cl.S([O-])(O)=[O:32].[Na+]>O.C(#N)C>[Cl:13][C:14]1[C:23]([C:24]([OH:32])=[O:25])=[C:22]([S:26]([CH3:29])(=[O:28])=[O:27])[CH:21]=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 5234Sodium ChlorideHCID 61488Phosphoric acid, disodium salt, hydrateHCID 18517410Methyl 2-chloro-3-formyl-4-methylsulfonylbenzoateHCID 23665763Sodium Bisulfite

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 a 30% strength solution of hydrogen peroxide and 66.2 g (0.59 mol) of an 80% strength aqueous sodium chloride solution were added successively 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 at 5° C. for 1 hour and then at room temperature for 12 hours. 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. The mixture was stirred at room temperature for 1 hour and the aqueous phase was extracted three times with ethyl acetate. The combined organic phases were washed with sodium hydrogen sulfite solution and dried. The solvent was distilled off, yielding 102.0 g of methyl 2-chloro-3-hydroxycarbonyl-4-methylsulfonylbenzoate.

Workup

  1. waitat room temperature for 12 hours
  2. additionwere added
  3. stirringThe mixture was stirred at room temperature for 1 hour
  4. extractionthe aqueous phase was extracted three times with ethyl acetate
  5. washThe combined organic phases were washed with sodium hydrogen sulfite solution
  6. customdried
  7. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-0f2f3b3e043b4135bb196d3103e24d0e
Source dataset
uspto-grants-2000_12
Patent number
US06165944

Reaction notes

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