Sodium Hydroxide → 5-Benzofuranacetic acid

HRID 37036Notes

Reaction equation

HRID 37036 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: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

4

Reactant 2

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

Product 1

HCID 234388925-Benzofuranacetic acidYield 99.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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. extractiondiluted-with water and extracted 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-e1f85173cb4b40e7912ff01baf9a6454
Source dataset
uspto-grants-1995_05
Patent number
US05420010

Reaction notes

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