Sodium Hydroxide → 1-(4-Fluorophenyl)-1,3-dihydroisobenzofuran-5-carboxylic acid

HRID 1596802

Reaktionsgleichung

Reaktionsgleichung von HRID 1596802
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]([O:19]CC)=[O:18])=[CH:14][CH:15]=3)[CH2:10][O:9]2)=[CH:4][CH:3]=1.[OH-].[Na+]>CCO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]([OH:19])=[O:18])=[CH:14][CH:15]=3)[CH2:10][O:9]2)=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 21703105Ethyl 1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carboxylate

Produkt 1

HCID 155384031-(4-Fluorophenyl)-1,3-dihydroisobenzofuran-5-carboxylic acidAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

Crude ethyl 1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carboxylat (30 g) is dissolved in EtOH (96%, 150 ml) and aqueous 2N NaOH (150 ml). The solution is refluxed for 1 hour. ½ of the volume is removed in vacuo. The aqueous phase is extracted with EtOAc (2×100 ml). The aqueous phase is made acidic (pH=1, conc. HCl) and after cooling to 5° C. the white crystals are filtered off. Yield 16 g. Overall yield is 66% starting from 5-ethoxycarbonylphthalide. Mp 187-190° C.

Aufarbeitung

  1. temperatureThe solution is refluxed for 1 hour
  2. custom½ of the volume is removed in vacuo
  3. extractionThe aqueous phase is extracted with EtOAc (2×100 ml)
  4. filtrationare filtered off

Quellen und Nachweise

ORD-Eintrag
ord-972e933fb03a43018afe59087d33f334
Quelldatensatz
uspto-grants-2001_09
Patentnummer
US06291689B1

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