Dimethyl Sulfoxide → Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, ethyl ester

Participants

Reaction Conditions

Reaction Steps

A mixture of diethyl-2-(2',2'-dichlorovinyl)-3,3-dimethyl-1,1-cyclopropane-dicarboxylate (5.0 g), sodium chloride (0.95 g), dimethylsulphoxide (12.0 ml) and water (0.6 ml) was heated to 175° C. under a nitrogen atmosphere and kept at this temperature for 9 hours. At the end of this time, the mixture was cooled to room temperature and poured into water (50 ml). The mixture was extracted with petroleum ether (boiling point 60° to 80° C.) and the extracts were dried over anhydrous magnesium sulphate. After removing the solvent by evaporating under reduced pressure, the residual oil was purified by distillation and ethyl 2-(2',2'-dichlorovinyl)-3,3-dimethyl-cyclopropane-carboxylate was obtained as a colorless liquid (boiling point 102° C./13.3 Pa) in a yield of 15-20% of theory. The identity of the compound was confirmed by comparing the IR spectrum with that of an authentic sample. The mixture contained the trans isomer and the cis isomer in a ratio of 55 to 45.

Provenance & Evidence