Potassium Hydroxide → Di-n-butyl 2-vinylcyclopropane-1,1-dicarboxylate

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Employing a reaction similar to that described in Example 1 except that a hydrocarbon solvent is included in the reaction mixture, 152 g 50% aqueous potassium hydroxide solution was added dropwise to a vigorously stirred solution of 64.5 g (0.52 mol) trans 1,4-dichlorobutene-2,112.5 g (0.52 mol) di-n-butyl malonate, 4.0 g tricaprylylmethylammonium chloride and 200 cc petroleum ether. Upon workup and distillation, 47.6 g (37.1% yield) of di-n-butyl 2-vinylcyclopropane-1,1-dicarboxylate (bp 101°-104° C. (0.30 mm)); nD24° 1.4556) was obtained. Infrared and proton nmr spectra were consistent with th desired vinylcyclopropane product. Attempts to carry out the reaction in the absence of the onium compound were unsuccessful.

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