Hydrochloric Acid → 4-Methoxy-1-benzofuran-2-carboxylic acid

HRID 2221446Notes

Reaction equation

HRID 2221446 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[CH:9]=[C:10]([C:12]([O:14]C)=[O:13])[O:11][C:7]=2[CH:6]=[CH:5][CH:4]=1.[OH-].[Na+].Cl>C1COCC1.CO.O.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[C:8]2[CH:9]=[C:10]([C:12]([OH:14])=[O:13])[O:11][C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22729192HCID 22729192, compound

Product 1

HCID 227289824-Methoxy-1-benzofuran-2-carboxylic acidYield 96%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a suspension of methyl 4-methoxy-benzofuran-2-ylcarboxylate (206 mg, 1.0 mmol) in THF/methanol/water (6 ml, 1/1/1) was added 2M aqueous NaOH (1.0 ml) and refluxed until saponification was completed (˜3 h). The reaction mixture was acidified with 1M aqueous HCl (10 ml) and diluted with ethyl acetate (30 ml). The separated organic layer was washed with 1M aqueous HCl (30 ml), brine (30 ml), dried over sodium sulfate, and concentrated in vacuo to provide 4-methoxy-benzofuran-2-ylcarboxylic acid as a white solid (189 mg, 0.96 mmol), which was used without further purification.

Workup

  1. temperaturerefluxed until saponification
  2. custom(˜3 h)
  3. washThe separated organic layer was washed with 1M aqueous HCl (30 ml), brine (30 ml)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-feac74690d5846dd8efa2c06e067b722
Source dataset
uspto-grants-2008_05
Patent number
US07368572B2

Reaction notes

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