Potassium Hydroxide → 1-(2-Methoxyphenyl)-3-(3,4-methylenedioxyphenyl)indane-2-carboxylic acid

HRID 650765Notes

Reaction equation

HRID 650765 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]([C:18]2[CH:23]=[CH:22][C:21]3[O:24][CH2:25][O:26][C:20]=3[CH:19]=2)[CH:10]1[C:27]([O-:29])=[O:28].[OH-].[K+]>CCO.C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]([C:18]2[CH:23]=[CH:22][C:21]3[O:24][CH2:25][O:26][C:20]=3[CH:19]=2)[CH:10]1[C:27]([OH:29])=[O:28]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 217147881-(2-Methoxyphenyl)-3-(3,4-methylenedioxyphenyl)indane-2-carboxylate

Product 1

HCID 187039001-(2-Methoxyphenyl)-3-(3,4-methylenedioxyphenyl)indane-2-carboxylic acidYield 49%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranCatalystHCID 702EthanolSolvent

Procedure

To a solution of ethyl (1RS, 2RS, 3RS)-1-(2-methoxyphenyl)-3-(3,4-methylenedioxyphenyl)indane-2-carboxylate (90 mg, 0.22 mmol) in EtOH (2 ml) containing a few drops of THF was added 6M KOH (0.22 ml, 1.32 mmol). The resulting mixture was allowed to stir at room temperature overnight, then was concentrated under reduced pressure. The residue was partitioned between H2O and Et2O. The aqueous phase was acidified with 3M HCl and extracted with EtOAc. The EtOAc extract was washed successively with H2O and saturated aqueous NaCl and dried (MgSO4). The solvent was removed in vacuo to afford the title compound (40 mg, 49%).

Workup

  1. concentrationwas concentrated under reduced pressure
  2. customThe residue was partitioned between H2O and Et2O
  3. extractionextracted with EtOAc
  4. extractionThe EtOAc extract
  5. washwas washed successively with H2O and saturated aqueous NaCl
  6. dry with materialdried (MgSO4)
  7. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-b40ed53f97e045bcaad14a5e3de661f5
Source dataset
uspto-grants-2001_08
Patent number
US06274737B1

Reaction notes

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