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

HRID 1067419Notes

Reaction equation

HRID 1067419 reaction equation
C[O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH2:11][C:12]([O:14]CC)=[O:13])[C:5]=1[O:17][CH2:18][C:19]([O:21]CC)=[O:20].[OH-].[Na+]>CO>[C:19]([CH2:18][O:17][C:5]1[C:6]([O:10][CH2:11][C:12]([OH:14])=[O:13])=[CH:7][CH:8]=[CH:9][C:4]=1[C:3]([OH:24])=[O:2])([OH:21])=[O:20]

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-6578c2becaf74040b731a50f0b1bf3dd
Source dataset
uspto-grants-2001_06
Patent number
US06248766B1

Reaction notes

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