Sulfuric Acid → Coumaranone

HRID 716728

Reaction equation

HRID 716728 reaction equation
C([O:4][C:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[O:7][CH:6]=1)(=O)C.OS(O)(=O)=O>CO>[O:7]1[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:5](=[O:4])[CH2:6]1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 27696211-Benzofuran-3-yl acetate

Product 1

HCID 23556CoumaranoneYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of benzofuran-3-yl acetate (8) (100 g, 1.42 mol) in methanol (350 mL) was added diluted (7.5%) H2SO4 (500 mL) at ambient temperature followed by heating to reflux for 1-3 h. The progress of the reaction was monitored by HPLC analysis. Upon completion of the reaction, the reaction mixture was cooled, filtered, and the slurry was washed with water, and vacuum dried to obtain the product meeting the desired specifications. Yield—83-100%.

Workup

  1. temperatureby heating
  2. temperatureto reflux for 1-3 h
  3. customUpon completion of the reaction
  4. temperaturethe reaction mixture was cooled
  5. filtrationfiltered
  6. washthe slurry was washed with water, and vacuum
  7. customdried
  8. customto obtain the product

Sources & evidence

ORD record
ord-69ad0f572a2c40928d1126551b4af5f7
Source dataset
uspto-grants-2015_11
Patent number
US09193698B2

Linked notes

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