Hydrochloric Acid → 2-Methoxy-5-methYlsulfinylbenzoic acid

HRID 323393Notes

Reaction equation

HRID 323393 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([S:13]([CH3:15])=[O:14])=[CH:9][C:4]=1[C:5]([O:7]C)=[O:6].[OH-].[K+].Cl>ClCCl>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([S:13]([CH3:15])=[O:14])=[CH:9][C:4]=1[C:5]([OH:7])=[O:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 18464431Methyl 2-methoxy-5-methylsulfinylbenzoate

Product 1

HCID 184645372-Methoxy-5-methYlsulfinylbenzoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Combine methyl 2-methoxy-5-methylsulfinylbenzoate (2.37 g, 12.0 mmol) and a 1 M aqueous solution of potassium hydroxide (13 mL, 13 mmol). Heat to reflux. After 2 hours, cool to ambient temperature and adjust the pH to about 2 using a 1 M aqueous hydrochloric acid (14.5 mL, 14.5 mmol. Evaporate in vacuo to give a solid. Combine the solid and dichloromethane and stir. Decant the solvent and add more dichloromethane. Again decant and combine with the first decantate, dry over Na2SO4, filter, and evaporate in vacuo to to give the title compound.

Workup

  1. temperatureHeat to reflux
  2. customEvaporate in vacuo
  3. customto give a solid
  4. customDecant the solvent
  5. additionadd more dichloromethane
  6. customAgain decant
  7. dry with materialdry over Na2SO4
  8. filtrationfilter
  9. customevaporate in vacuo

Sources & evidence

ORD record
ord-397b5f115d4e43bf90dbbdbb031c65c9
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

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