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Potassium Hydroxide → 1-(3,4-Methylenedioxyphenyl)-3-phenylindane-2-carboxylic acid

HRID 862938
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 862938
[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][CH:22]=[CH:21][CH:20]=4)[CH:11]3[C:25]([O:27]CC)=[O:26])=[CH:4][C:3]=2[O:2]1.[OH-].[K+]>CCO.C1COCC1>[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:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH:11]3[C:25]([OH:27])=[O:26])=[CH:4][C:3]=2[O:2]1
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Komponenten

5

Edukt 2

HCID 14797Potassium HydroxideHCID 53834977Ethyl (RS)-1-(3,4-Methylenedioxyphenyl)-3-phenylindane-2-carboxylate

Produkt 1

HCID 217147901-(3,4-Methylenedioxyphenyl)-3-phenylindane-2-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of ethyl(1RS,2SR,3SR)-1-(3,4-methylenedioxyphenyl)-3-phenylindane-2-carboxylate (650 mg, 1.68 mmol) in EtOH containing a few drops of THF was added 6M KOH (1.68 ml, 10.1 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 several times with EtOAc. The combined EtOAc extracts were washed successively with H2O and saturated aqueous NaCl and dried (MgSO4). The solvent was removed in vacuo to afford an oil, which was crystallized from EtOAc/hexanes. The title compound was obtained as a solid (305 mg, 51%); m.p. 186°-187° C.

Aufarbeitung

  1. concentrationwas concentrated under reduced pressure
  2. customThe residue was partitioned between H2O and Et2O
  3. extractionextracted several times with EtOAc
  4. washThe combined EtOAc extracts were washed successively with H2O and saturated aqueous NaCl
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed in vacuo
  7. customto afford an oil, which
  8. customwas crystallized from EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-2d3cb0cea6cd4c738b6f26d3cfb9e876
Quelldatensatz
uspto-grants-1998_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05719182

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