Sodium Hydroxide → 2,3-Bis(carboxymethoxy)benzoic acid

HRID 2228673Notes

Reaction equation

HRID 2228673 reaction equation
C([O:3][C:4]([CH2:6][O:7][C:8]1[C:17]([O:18][CH2:19][C:20]([O:22]CC)=[O:21])=[CH:16][CH:15]=[CH:14][C:9]=1[C:10]([O:12]C)=[O:11])=[O:5])C.[OH-].[Na+]>CO>[C:4]([CH2:6][O:7][C:8]1[C:17]([O:18][CH2:19][C:20]([OH:22])=[O:21])=[CH:16][CH:15]=[CH:14][C:9]=1[C:10]([OH:12])=[O:11])([OH:5])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 53707402HCID 53707402, compound

Product 1

HCID 220338052,3-Bis(carboxymethoxy)benzoic acidYield 68.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl [2,3-bis(ethoxycarbonylmethoxy)]benzoate (58.0 g, 170 mmol) in methanol (100 mL) at 60° C. was added 3N-aqueous sodium hydroxide solution over 30 minutes, and the reaction mixture was refluxed for 2 hours. The solvent was then distilled off under reduced pressure. To that residue was added 4N-hydrochloric acid. The crystal was collected with filtration, and dried to provide 31.3 g of the title compound. Yield 68%.

Workup

  1. temperaturethe reaction mixture was refluxed for 2 hours
  2. distillationThe solvent was then distilled off under reduced pressure
  3. additionTo that residue was added 4N-hydrochloric acid
  4. filtrationThe crystal was collected with filtration
  5. customdried

Sources & evidence

ORD record
ord-eb4206cb89204321a084832fb57ed324
Source dataset
uspto-grants-2002_07
Patent number
US06417213B2

Reaction notes

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