Sodium Hydroxide → 3-(2-Methoxyethoxy)-2-methyl-4-(methylsulfonyl)benzoic acid

HRID 1642012Notes

Reaction equation

HRID 1642012 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[C:7]([CH3:20])=[C:8]([CH:13]=[CH:14][C:15]=1[S:16]([CH3:19])(=[O:18])=[O:17])[C:9]([O:11]C)=[O:10].[OH-].[Na+]>CO>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[C:7]([CH3:20])=[C:8]([CH:13]=[CH:14][C:15]=1[S:16]([CH3:19])(=[O:17])=[O:18])[C:9]([OH:11])=[O:10]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66755969Methyl 3-(2-methoxyethoxy)-2-methyl-4-(methylsulfonyl)benzoate

Product 1

HCID 667565243-(2-Methoxyethoxy)-2-methyl-4-(methylsulfonyl)benzoic acidYield 78.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 3-(2-methoxyethoxy)-2-methyl-4-(methylsulfonyl)benzoate (26 g) was dissolved in methanol (200 mL), and a 20% NaOH aqueous solution (50 mL) was added at room temperature. After stirring for one hour, methanol was distilled off under reduced pressure. To the residue, 2N hydrochloric acid (100 mL) was added, followed by extraction with ethyl acetate (500 mL). The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate, and then, the solvent was distilled off under reduced pressure. To the residue, a mixed solvent (ethyl acetate:hexane=1:1, 50 mL) was added, and the mixture was left to stand at 5° C. for 12 hours. The obtained crystals were collected by filtration to obtain 3-(2-methoxyethoxy)-2-methyl-4-(methylsulfonyl)benzoic acid (19.5 g).

Workup

  1. distillationmethanol was distilled off under reduced pressure
  2. additionTo the residue, 2N hydrochloric acid (100 mL) was added
  3. extractionfollowed by extraction with ethyl acetate (500 mL)
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. additionTo the residue, a mixed solvent (ethyl acetate:hexane=1:1, 50 mL) was added
  8. waitthe mixture was left
  9. waitto stand at 5° C. for 12 hours
  10. filtrationThe obtained crystals were collected by filtration

Sources & evidence

ORD record
ord-65f0b49619694cacb2a38a97ba849a80
Source dataset
uspto-grants-2012_02
Patent number
US08119569B2

Reaction notes

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