Acetic Anhydride → Methyl benzofuran-7-carboxylate

HRID 1761930Notes

Reaction equation

HRID 1761930 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:15]=[CH:14][CH:13]=[C:12]([CH:16]=O)[C:6]=1[O:7][CH2:8]C(O)=O)=[O:4].C([O-])(=O)C.[Na+].C(OC(=O)C)(=O)C.C(=O)([O-])[O-].[K+].[K+]>O>[O:7]1[C:6]2[C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:15][CH:14]=[CH:13][C:12]=2[CH:16]=[CH:8]1

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 11430Potassium CarbonateHCID 517045Sodium AcetateHCID 20043642HCID 20043642, compound

Product 1

HCID 14229730Methyl benzofuran-7-carboxylateYield 25.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2.09 g of (2-methoxycarbonyl-6-formylphenoxy)acetic acid, 1.48 g of sodium acetate and 7 ml of acetic anhydride is refluxed for 1.5 hours. After cooling, water is added to the reaction mixture, and the aqueous mixture is alkalized with potassium carbonate and extracted with ethyl acetate. The extract is washed with water, dried and evaporated to remove solvent. The residue is purified by silica gel column chromatography to give 0.39 g of methyl benzofuran-7-carboxylate as colorless oil.

Workup

  1. temperatureis refluxed for 1.5 hours
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  4. washThe extract is washed with water
  5. customdried
  6. customevaporated
  7. customto remove solvent
  8. customThe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-26d14820452b407593991de30db3ffae
Source dataset
uspto-grants-1989_05
Patent number
US04829067

Reaction notes

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