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

HRID 1661959Notes

Reaction equation

HRID 1661959 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 87.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 3-(2-methoxyethoxy)-2-methyl-4-(methylsulfonyl)benzoate (680 mg, 2.25 mmol) was dissolved in methanol (10 mL), and an aqueous sodium hydroxide solution (2 mL) at a concentration of 20% was added thereto at room temperature. After stirring for 30 minutes, the solvent was removed under reduced pressure. 100 mL of 1N hydrochloric acid was added to the residue, followed by extraction with ethyl acetate (200 mL). The organic layer was washed twice with a saturated brine and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 3-(2-methoxyethoxy)-2-methyl-4-(methylsulfonyl)benzoic acid (570 mg) as a white solid.

Workup

  1. customat room temperature
  2. customthe solvent was removed under reduced pressure
  3. addition100 mL of 1N hydrochloric acid was added to the residue
  4. extractionfollowed by extraction with ethyl acetate (200 mL)
  5. washThe organic layer was washed twice with a saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-2c5f5a0b6d7e46f6aee61ddc036a22c7
Source dataset
uspto-grants-2011_10
Patent number
US08030498B2

Reaction notes

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