Sodium Hydroxide → 3-(Methoxycarbonyl)benzoic acid

HRID 2105181Notes

Reaction equation

HRID 2105181 reaction equation
[C:1]([O:13]C)(=[O:12])[C:2]1[CH:11]=[CH:10][CH:9]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[CH:3]=1.[OH-].[Na+]>CC(C)=O.CO>[CH3:8][O:7][C:5](=[O:6])[C:4]1[CH:9]=[CH:10][CH:11]=[C:2]([C:1]([OH:13])=[O:12])[CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 15088Dimethyl isophthalate

Product 1

HCID 6018803-(Methoxycarbonyl)benzoic acidYield 73%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 887MethanolSolvent

Procedure

A solution of dimethyl isophthalate (25 g, 128.75 mmol) was dissolved in acetone (250 mL) and a solution of NaOH (5.4 g, 135 mmol) in methanol (50 mL) was added dropwise. A white precipitated was observed and the slurry was stirred for 18 h at room temperature. Then powdered NaOH (0.5 g) was added. The acetone was evaporated until dryness and the white residue was dissolved in water (250 mL), extracted with diethylether (2×100 mL). The aqueous solution was acidified with concentrated HCl to pH 4˜5 and the white precipitate was filtered, dried under vacuum and the desired monoacid obtained (17 g, 94.36 mmol, 73% yield) as a white solid.

Workup

  1. customA white precipitated
  2. additionThen powdered NaOH (0.5 g) was added
  3. customThe acetone was evaporated until dryness
  4. dissolutionthe white residue was dissolved in water (250 mL)
  5. extractionextracted with diethylether (2×100 mL)
  6. filtrationthe white precipitate was filtered
  7. customdried under vacuum
  8. customthe desired monoacid obtained (17 g, 94.36 mmol, 73% yield) as a white solid

Sources & evidence

ORD record
ord-0abbaf8ec1df4bd49ee0779479ea3afe
Source dataset
uspto-grants-2009_08
Patent number
US07579350B2

Reaction notes

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