Hydrochloric Acid → 2-Methoxy-5-methYlsulfinylbenzoic acid

HRID 637127Notes

Reaction equation

HRID 637127 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: 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 dichloromethane
  6. customAgain decant
  7. dry with materialdry over Na2SO4
  8. filtrationfilter
  9. customevaporate in vacuo
  10. customto to give the -title compound

Sources & evidence

ORD record
ord-0bc6a09d6f584264a63879474e9b34af
Source dataset
uspto-grants-2001_02
Patent number
US06194406B1

Reaction notes

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