Ethyl 3-(3,4-methylenedioxyphenyl)1-oxoindene-2-carboxylate → 1-(4-Methoxyphenyl)-3-(3,4-methylenedioxyphenyl)indane-2-carboxylic acid

HRID 650392Notes

Reaction equation

HRID 650392 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([C:10]3[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[C:12](=O)[C:11]=3[C:20]([O:22]CC)=[O:21])=[CH:4][C:3]=2[O:2]1>C([O-])([O-])=O.[Na+].[Na+]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:12]2[C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:10]([C:5]3[CH:6]=[CH:7][C:8]4[O:9][CH2:1][O:2][C:3]=4[CH:4]=3)[CH:11]2[C:20]([OH:22])=[O:21])=[CH:7][CH:8]=1

Participants

3

Reactant 1

HCID 18427631Ethyl 3-(3,4-methylenedioxyphenyl)1-oxoindene-2-carboxylate

Product 1

HCID 159085001-(4-Methoxyphenyl)-3-(3,4-methylenedioxyphenyl)indane-2-carboxylic acidYield 100%

Reagents, catalysts & solvents 1

HCID 10340Sodium CarbonateSolvent

Procedure

Ethyl 3-(3,4-Methylenedioxyphenyl)-1-oxoindene-2-carboxylate. A solution containing diethyl 2-[2-(3,4-methylenedioxybenzoyl)benzoylmalonate (crude material prepared above) in 5% aqueous Na2CO3 (100 ml) was heated at reflux for 10 min. The reaction mixture was then allowed to cool, and the aqueous material was removed by decantation. The residue was placed in H2O (50 ml), and the mixture was heated at reflux, cooled and concentrated under reduced pressure. The residue was recrystallized from hexanes to afford the title compound as a yellow solid (5.0 g, 100% for two steps).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 10 min
  3. temperatureto cool
  4. customthe aqueous material was removed by decantation
  5. temperaturethe mixture was heated
  6. temperatureat reflux
  7. temperaturecooled
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was recrystallized from hexanes

Sources & evidence

ORD record
ord-fbd296bfe93f4fb48834e63c0e16ad25
Source dataset
uspto-grants-2001_08
Patent number
US06271399B1

Reaction notes

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