Sulfuric Acid → 2-(6-Hydroxy-1-benzofuran-3-yl)acetic acid

HRID 1163291Notes

Reaction equation

HRID 1163291 reaction equation
Cl[CH2:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([OH:13])=[CH:10][CH:11]=2)[O:6][C:5](=[O:14])[CH:4]=1.S(=O)(=O)(O)[OH:16]>[OH-].[Na+]>[OH:13][C:9]1[CH:10]=[CH:11][C:12]2[C:3]([CH2:4][C:5]([OH:14])=[O:16])=[CH:2][O:6][C:7]=2[CH:8]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 53988464-(chloromethyl)-7-hydroxy-2H-chromen-2-one

Product 1

HCID 21109152-(6-Hydroxy-1-benzofuran-3-yl)acetic acidYield 83%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 4-(chloromethyl)-7-hydroxy-2H-chromen-2-one (10.9 g, 51.8 mmol) and 1 M aqueous sodium hydroxide solution (500 mL) was heated under reflux for 2 hr. The reaction mixture was allowed to cool, acidified with conc. sulfuric acid and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give (6-hydroxy-1-benzofuran-3-yl)acetic acid (8.27 g, 83%) as brown crystals.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hr
  3. temperatureto cool
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6b948c81283f468880cddeadc1a3e901
Source dataset
uspto-grants-2010_10
Patent number
US07820837B2

Reaction notes

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