4-Hydroxybenzaldehyde → HCID 60884381, Verbindung

HRID 562930

Reaktionsgleichung

Reaktionsgleichung von HRID 562930
F[C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:10][O:9]2)=[CH:4][CH:3]=1.[OH:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[CH:14][CH:13]=1.[OH-].[Na+]>C1(C)C=CC=CC=1>[OH:9][CH:8]([C:5]1[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=1)[CH2:10][O:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[CH:14][CH:13]=1

Komponenten

5

Edukt 3

HCID 1264-HydroxybenzaldehydeHCID 14798Sodium HydroxideHCID 40652302-(4-Fluorophenyl)oxirane

Produkt 1

HCID 60884381HCID 60884381, VerbindungAusbeute 14,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
78 °C

Versuchsvorschrift

To 2-(4-fluorophenyl)oxirane (6.50 g, 54.0 mmol) was added toluene (85 ml), 4-hydroxybenzaldehyde (9.89 g, 81.0 mmol), PEG4000 (polyethylene glycol, 1.15 g) and 1M NaOH (85 ml) and the stirring mixture was heated at 78° C. overnight. After cooling to RT the reaction mixture was extracted with EtOAc, and the organic phase was washed with brine, dried (Na2SO4), filtered and evaporated in vacuo. The resulting yellow oil was chromatographed on a medium silica gel column eluting with 0-10% EtOAc/DCM. Fractions containing predominantly the higher Rf spot were combined and evaporated in vacuo to give 1.85 g (14%) of the title compound as a yellow oil. Fractions containing predominantly the lower Rf spot were combined and evaporated in vacuo to give 0.64 g of the regioisomer as a colorless, viscous oil. Mixed fractions were combined and rechromatographed eluting with 30% EtOAc/hexanes. Fractions containing the higher Rf material were combined and evaporated in vacuo to give an additional 2.64 g (20%) of the title compound as a colorless oil. Fractions containing the lower Rf material were combined and evaporated in vacuo to give an additional 1.82 g of the regioisomer as a colorless viscous oil.

Aufarbeitung

  1. temperatureAfter cooling to RT the reaction mixture
  2. extractionwas extracted with EtOAc
  3. washthe organic phase was washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe resulting yellow oil was chromatographed on a medium silica gel column
  8. washeluting with 0-10% EtOAc/DCM
  9. additionFractions containing predominantly the higher Rf spot
  10. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a095e2121563486dabe01d46a5c2e3d9
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08067450B2

Verknüpfte Notizen

Wird geladen…