Sulfuric Acid → HCID 22387841, compound

HRID 1072812Notes

Reaction equation

HRID 1072812 reaction equation
[C:1]([C:4]1[CH:13]=[CH:12][C:7]2[O:8][C:9]([CH3:11])=[CH:10][C:6]=2[CH:5]=1)([OH:3])=[O:2].S(=O)(=O)(O)O.[C:19](=O)([O-])O.[Na+]>CO>[CH3:19][O:2][C:1]([C:4]1[CH:13]=[CH:12][C:7]2[O:8][C:9]([CH3:11])=[CH:10][C:6]=2[CH:5]=1)=[O:3]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 10921182-methyl-1-benzofuran-5-carboxylic acid

Product 1

HCID 22387841HCID 22387841, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Carboxy-2-methylbenzo[b]furan (1.9 g, 10.7 mmol) was suspended in methanol (50 ml) and concentrated sulfuric acid (0.1 ml) was added, which was followed by reflux under heating for 14 hr. After cooling, a saturated aqueous sodium hydrogencarbonate solution was added. Methanol was evaporated under reduced pressure, and the residue was extracted with methyl t-butyl ether. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The desiccant was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=9/1) to give the objective compound (1.66 g, 81%) as colorless crystals.

Workup

  1. temperatureby reflux
  2. temperatureunder heating for 14 hr
  3. temperatureAfter cooling
  4. customMethanol was evaporated under reduced pressure
  5. extractionthe residue was extracted with methyl t-butyl ether
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationThe desiccant was filtered off
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-22a2ced5e5a44c688f1f217b317f00b0
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

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