Sodium Hydroxide → (1RS,3RS)-1,3-Di-(3,4-methylenedioxyphenyl)indane-2-carboxylic acid

HRID 863124Notes

Reaction equation

HRID 863124 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH:10]3[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[CH:12]([C:19]4[CH:24]=[CH:23][C:22]5[O:25][CH2:26][O:27][C:21]=5[CH:20]=4)[CH:11]3[C:28]([O:30]CC)=[O:29])=[CH:4][C:3]=2[O:2]1.[OH-].[Na+]>CCO>[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH:10]3[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[CH:12]([C:19]4[CH:24]=[CH:23][C:22]5[O:25][CH2:26][O:27][C:21]=5[CH:20]=4)[CH:11]3[C:28]([OH:30])=[O:29])=[CH:4][C:3]=2[O:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18969665ethyl(1RS,3RS)-1,3-di-(3,4-methylenedioxyphenyl)indane-2-carboxylate

Product 1

HCID 10135727(1RS,3RS)-1,3-Di-(3,4-methylenedioxyphenyl)indane-2-carboxylic acidYield 73.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl (1RS,3RS)-1,3-di-(3,4-methylenedioxyphenyl)indane-2-carboxylate (75 mg, 0.17 mmol) in EtOH (20 ml) was added NaOH (0.10 g, 2.5 mmol). The resulting mixture was allowed to stir at room temperature for 3 d, at which time thin layer chromatographic analysis indicated that the reaction was incomplete. The mixture was then heated at reflux for 36 h, allowed to cool and was concentrated under reduced pressure. To the residue was added concentrated HCl, and the solid which formed was collected by filtration and dried. The solid was triturated with boiling hexanes to afford the title compound as a white solid (50 mg, 73%); m.p. 182°-185° C.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureat reflux for 36 h
  3. temperatureto cool
  4. concentrationwas concentrated under reduced pressure
  5. additionTo the residue was added concentrated HCl
  6. customthe solid which formed
  7. filtrationwas collected by filtration
  8. customdried
  9. customThe solid was triturated with boiling hexanes

Sources & evidence

ORD record
ord-f682f4c67df1452db77662f1750ae32f
Source dataset
uspto-grants-1998_02
Patent number
US05719183

Reaction notes

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