Sulfuric Acid → HCID 11229474, compound

HRID 430739Notes

Reaction equation

HRID 430739 reaction equation
[CH3:1][O:2][C:3]1[C:11]2[O:10][C:9]([CH2:16][CH:17]=[CH2:18])(C(OC)=O)[C:8](=[O:19])[C:7]=2[CH:6]=[CH:5][CH:4]=1.S(=O)(=O)(O)O.C(=O)([O-])O.[Na+]>C(O)(C)(C)C>[CH3:1][O:2][C:3]1[C:11]2[O:10][CH:9]([CH2:16][CH:17]=[CH2:18])[C:8](=[O:19])[C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 11448389HCID 11448389, compound

Product 1

HCID 11229474HCID 11229474, compoundYield 79.4%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

Methyl 7-methoxy-3-oxo-2-(2-propenyl)-2,3-dihydrobenzofuran-2-carboxylate (18.42 g) and concentrated sulfuric acid (2 ml) were dissolved in t-butyl alcohol (150 ml) and the solution was refluxed for 22.5 hours. After cooling the reaction solution to room temperature, the reaction solution was neutralized with saturated aqueous sodium hydrogen carbonate and then washed with saturated brine, followed by drying the resultant over sodium sulfate. After removing sodium sulfate by filtration, the solvent was evaporated under reduced pressure, and the residue was purified by column chromatography (solvent:hexane/ethyl acetate=4/1) using silica gel to obtain the desired compound (11.39 g, yield: 79%).

Workup

  1. temperaturethe solution was refluxed for 22.5 hours
  2. washwashed with saturated brine
  3. dry with materialby drying the resultant over sodium sulfate
  4. customAfter removing sodium sulfate
  5. filtrationby filtration
  6. customthe solvent was evaporated under reduced pressure
  7. customthe residue was purified by column chromatography (solvent:hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-fdf58d09aee14aed8abb2104603372dd
Source dataset
uspto-grants-2001_11
Patent number
US06323235B1

Reaction notes

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