Triethylene glycol divinyl ether → 4-Methyl-3-(4-methylphenyl)-4-pentenal

HRID 2387592

Reaktionsgleichung

Reaktionsgleichung von HRID 2387592
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](O)[C:9]([CH3:11])=[CH2:10])=[CH:4][CH:3]=1.[CH2:13]=[CH:14][O:15]CCOCCOCCOC=C>C([O-])(=O)C.[Hg+2].C([O-])(=O)C>[CH3:11][C:9](=[CH2:10])[CH:8]([C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=1)[CH2:13][CH:14]=[O:15]

Komponenten

4

Edukt 2

HCID 3033992Triethylene glycol divinyl etherHCID 540233242-Methyl-1-(4-methylphenyl)prop-2-en-1-ol

Produkt 1

HCID 873705594-Methyl-3-(4-methylphenyl)-4-pentenalAusbeute 45,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 15337Mercuric acetateKatalysator

Versuchsvorschrift

(3E)-(4-Methylphenyl)-2-methyl-2-propen-1-ol (17.33 g, 0.102 mol), tri (ethylene glycol) divinyl ether (Aldrich 98%, 20.5 g, 0.102 mol) and mercury(II) acetate (1 g, 0.003 mol) were heated together under nitrogen at 155-160° C. (bath temperature) for 3 hours. After cooling to room temperature, the reaction was diluted with heptanes, washed with water (3 times). Each aqueous phase was re-extracted with heptanes. Combined extracts were dried over solid anhydrous sodium sulfate. The solid was filtered off, rinsed with heptanes and the solvent was removed under vacuum. The crude product was purified by column chromatography on silica gel (eluent: heptanes/ethyl acetate (11:1) followed by bulb-to-bulb distillation (81° C./0.002 mbar). 8.71 g of the desired product were obtained (yield=43%).

Aufarbeitung

  1. washwashed with water (3 times)
  2. extractionEach aqueous phase was re-extracted with heptanes
  3. dry with materialCombined extracts were dried over solid anhydrous sodium sulfate
  4. filtrationThe solid was filtered off
  5. washrinsed with heptanes
  6. customthe solvent was removed under vacuum
  7. customThe crude product was purified by column chromatography on silica gel (eluent
  8. distillationheptanes/ethyl acetate (11:1) followed by bulb-to-bulb distillation (81° C./0.002 mbar)

Quellen und Nachweise

ORD-Eintrag
ord-9151c505dcbf4730b0a2e6c2ab9135d9
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08268895B2

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