Water → 1-(4-Methoxyphenyl)-3-phenylindane-2-carboxylic acid

HRID 863104Notes

Reaction equation

HRID 863104 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:10]2[C:24]([O:26]CC)=[O:25])=[CH:5][CH:4]=1.[OH-].[Na+].O>CCO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:10]2[C:24]([OH:26])=[O:25])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 67643697Ethyl(1RS,2SR,3SR)-1-(4-Methoxyphenyl)-3-phenylindane-2-carboxylate

Product 1

HCID 159084991-(4-Methoxyphenyl)-3-phenylindane-2-carboxylic acidYield 83.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl (1RS,2SR,3SR)-1-(4-methoxyphenyl)-3-phenylindane-2-carboxylate, (5.5 g, 14.8 mmol) in EtOH (70 ml) was added 5M NaOH (9 ml, 45 mmol). The resulting mixture was stirred under an argon atmosphere for 1 d, at which time H2O (70 ml) was added. The mixture was concentrated under reduced pressure. The aqueous residue was extracted with Et2O, and the Et2O extracts were discarded. The aqueous phase was acidified with 6M HCl and extracted several times with EtOAc. The combined EtOAc extracts were washed successively with H2O and saturated aqueous NaCl and dried. The solvent was removed in vacuo to provide an oily residue which crystallized upon standing. The solid material was recrystallized from EtOAc/hexanes to afford the title compound (4.25 g, 83%); m.p. 164°-166° C.

Workup

  1. additionwas added
  2. concentrationThe mixture was concentrated under reduced pressure
  3. extractionThe aqueous residue was extracted with Et2O
  4. extractionextracted several times with EtOAc
  5. washThe combined EtOAc extracts were washed successively with H2O and saturated aqueous NaCl
  6. customdried
  7. customThe solvent was removed in vacuo
  8. customto provide an oily residue which
  9. customcrystallized
  10. customThe solid material was recrystallized from EtOAc/hexanes

Sources & evidence

ORD record
ord-caa503fd31de4158a84925e384bf846a
Source dataset
uspto-grants-1998_02
Patent number
US05719183

Reaction notes

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