Hydroquinone → Methyl (5-benzyl-3-furyl)methyl 2-vinylcyclopropane-1,1-dicarboxylate

Participants

Reaction Steps

Twenty grams (0.106 mol) (5-benzyl-3-furyl)carbinol was charged to a stirred glass reactor with 39 g (0.212 mol) dimethyl 2-vinylcyclopropane-1,1-dicarboxylate, 0.5 g hydroquinone, 0.5 g calcium acetate and 0.38 g dibutyltin diacetate and heated. After the temperature reached about 165° C., methanol began to distill from the reaction mixture and was collected by means of a suitable condenser-trap arrangement. When the transalcoholysis was essentially complete (3.2 g methanol collected; reaction temperature 182° C.) heating was terminated. Excess dimethyl 2-vinylcyclopropane-1,1-dicarboxylate was removed by distillation and the resulting crude light brown oil worked up to recover 12.6 g (35% yield) methyl (5-benzyl-3-furyl)methyl 2-vinylcyclopropane-1,1-dicarboxylate. B.p. 160°-162° C. at 0.018 mm Hg; nD21 1.5335. Infrared and nuclear magnetic resonance spectra were consistent with the desired structure.

Provenance & Evidence