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

HRID 862327Notes

Reaction equation

HRID 862327 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 concentrat-ed 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 and concentrat-ed under reduced pressure
  8. customThe residue was recrystallized from hexanes

Sources & evidence

ORD record
ord-6fde6a2b03364a3488c0cb9306fb3dc5
Source dataset
uspto-grants-1998_02
Patent number
US05716984

Reaction notes

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