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

Participants

Reaction Steps

(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%).

Provenance & Evidence