Hydrochloric Acid → 2-Methoxy-5-methYlsulfinylbenzoic acid

HRID 2230599Notes

Reaction equation

HRID 2230599 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 dicliloromethane. Again decant and combine with the first decantate, dry over Na2SO4, filter, and evaporate in vacuo to to give the title compound: mp; 114-116° C.

Workup

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

Sources & evidence

ORD record
ord-3bc802bb233041aabd0107d7db0ff7b3
Source dataset
uspto-grants-2002_07
Patent number
US06423704B1

Reaction notes

Loading…