Reaktion #549762

Reaktionsgleichung

ethyl 2-vinyl-1-benzoylcyclopropane-1-carboxylate

tricaprylylmethylammonium chloride

cyclopropyl ketone

→

4-carbethoxy-5-phenyl-2-vinyl-2,3-dihydrofuran

Reaktionsbedingungen

Vorschrift

4-Carbethoxy-5-phenyl-2-vinyl-2,3-dihydrofuran was obtained in the usual manner by isomerizing ethyl 2-vinyl-1-benzoylcyclopropane-1-carboxylate. To catalyze the isomerization, tricaprylylmethylammonium chloride was employed at a 20 percent weight level. The mixture was heated at 150° C. for about two hours after which time only about 7 percent of the cyclopropyl ketone remained. After two distillations of the resulting isomerized product, essentially pure 4-carbethoxy-5-phenyl-2-vinyl-2,3-dihydrofuran was obtained (B.P. 110° C. @ 0.1 mm Hg; nD25° 1.5570). The product had a pleasing aroma that was somewhat coumarin-like in odor character.

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