Furfuryl Alcohol → HCID 54101908, compound

Participants

Reaction Steps

A transalcoholysis reaction was carried out in a manner similar to that described for Example II using dimethyl 2-vinylcyclopropane-1,1-dicarboxylate (92 g; 0.5 mol) and furfuryl alcohol (24.5 g; 0.25 mol). When essentially all of the furfuryl alcohol was consumed, the reaction mixture was dissolved in ethyl ether and washed with aqueous potassium hydroxide (5%). The ether portion was dried over MgSO4, filtered and vacuum distilled to obtain 21.63 g crude methyl (2-furyl)methyl 2-vinylcyclopropane-1,1-dicarboxylate. B.p. 91°-97° C. at 0.015 mm Hg. The distilled product (M.p. 58°-64° C.) was first recrystallized from methanol and then from a mixture of petroleum ether and methanol to obtain high purity methyl (2-furyl)methyl 2-vinylcyclopropane-1,1-dicarboxylate (translucent crystals melting at 67.5°-68.5° C.). The infrared spectra and nuclear magnetic resonance spectra were consistent with the desired product. Similar results are obtained when (5-methyl-2-furyl)carbinol, (5-allyl-3-furyl)carbinol and 5-hydroxymethyl-2,2'-difuryl methane are substituted for the furfuryl alcohol in the above reaction and all of these products are useful in insecticidal formulations.

Provenance & Evidence