Sodium Hydroxide → 5-Benzofuranacetic acid

HRID 483963Notes

Reaction equation

HRID 483963 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][C:11]([O:13]C)=[O:12])=[CH:9][C:4]=2[CH:3]=[CH:2]1.[OH-].[Na+]>CO.O>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][C:11]([OH:13])=[O:12])=[CH:9][C:4]=2[CH:3]=[CH:2]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 19748760Methyl 2-(benzofuran-5-YL)acetate

Product 1

HCID 234388925-Benzofuranacetic acidYield 99.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Methyl benzofuran-5-ylacetate (1.2 gm, 6.3 mmol) was dissolved in methanol (10 mL) and 2N sodium hydroxide (6.5 mL) was added under nitrogen and the mixture was stirred at rt for 3 hr. It was then diluted with water and extracted with ether. The aqueous layer was acidified with 2N hydrochloric acid and again extracted twice with ethyl acetate. The organic layers were washed with brine, combined, dried over sodium sulfate and evaporated to give 1.1 gm of title compound suitable for the next step.

Workup

  1. extractionextracted with ether
  2. extractionagain extracted twice with ethyl acetate
  3. washThe organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-ea0182c2e6d048ecb6700e6956c5eb18
Source dataset
uspto-grants-1993_07
Patent number
US05229267

Reaction notes

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