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

HRID 453434Notes

Reaction equation

HRID 453434 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

4-(Chloromethyl)-7-hydroxy-2H-chromen-2-one (10.9 g, 51.8 mmol) was dissolved in 1 M aqueous sodium hydroxide solution (500 mL), and the mixture was heated under reflux for 2 hr. The reaction mixture was allowed to cool, acidified with concentrated 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 the title compound (8.27 g, yield 83%) as brown crystals.

Workup

  1. temperaturethe mixture was 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-13f639c0b4e34d6bb8a98bacd5bd5da3
Source dataset
uspto-grants-2013_07
Patent number
US08492430B2

Reaction notes

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