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

HRID 399197
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 399197
[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
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

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

Produkt 1

HCID 159084991-(4-Methoxyphenyl)-3-phenylindane-2-carboxylic acidAusbeute 83,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

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 SM 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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-2c31e2e13e1a41d69a7c4dc39453741f
Quelldatensatz
uspto-grants-1998_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05817693

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