4-[2-(1,3-Dioxolan-2-yl)ethoxy]benzaldehyde → 2-[2-(4-Ethenylphenoxy)ethyl]-1,3-dioxolane

HRID 1377892

Reaktionsgleichung

Reaktionsgleichung von HRID 1377892
[CH3:1]C(C)([O-])C.[K+].[O:7]1[CH2:11][CH2:10][O:9][CH:8]1[CH2:12][CH2:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CCOCC>[CH:19]([C:18]1[CH:21]=[CH:22][C:15]([O:14][CH2:13][CH2:12][CH:8]2[O:9][CH2:10][CH2:11][O:7]2)=[CH:16][CH:17]=1)=[CH2:1]

Komponenten

5

Edukt 2

HCID 196934664-[2-(1,3-Dioxolan-2-yl)ethoxy]benzaldehydeHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 196934692-[2-(4-Ethenylphenoxy)ethyl]-1,3-dioxolaneAusbeute 88,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74505Methyltriphenyliphosphonium bromideKatalysatorHCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

In another 2 liter flask, 57.2 g of methyl triphenylphosphonium bromide was placed. 500 ml of anhydrous ether was poured and then, stirred. To the resulting solution was slowly added 18.0 g of potassium tert-butoxide and reacted at room temperature for 3 hrs. 23.7 g of the above 4-(2-[1,3]-dioxolan-2-yl-ethoxy)benzaldehyde was dissolved in 200 ml of anhydrous ether and was slowly added to the reaction mixture and then subjected to reaction at room temperature for 4 hrs. After completion of the reaction, the produced solid by-product was filtered off and washed with distilled water and saturated saline. The organic phase washed was dried over anhydrous magnesium sulfate and the solvent was removed by distillation under reduced pressure. The reaction mixture was purified by Silica gel column chromatography to obtain 20.8 g of 2-[2-(4-vinylphenoxy)ethyl]-[1,3]-dioxolan, represented by the following formula: ##STR10##

Aufarbeitung

  1. customreacted at room temperature for 3 hrs
  2. additionwas slowly added to the reaction mixture
  3. customsubjected to reaction at room temperature for 4 hrs
  4. customAfter completion of the reaction
  5. filtrationthe produced solid by-product was filtered off
  6. washwashed with distilled water and saturated saline
  7. washThe organic phase washed
  8. dry with materialwas dried over anhydrous magnesium sulfate
  9. customthe solvent was removed by distillation under reduced pressure
  10. customThe reaction mixture was purified by Silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-af980823728e4f8c87a68b0a989d523f
Quelldatensatz
uspto-grants-1997_09
Patentnummer
US05665841

Verknüpfte Notizen

Wird geladen…