Thionyl Chloride → rel-(1R,3R)-3-[(1Z)-2-Chloro-2-(4-chlorophenyl)ethenyl]-2,2-dimethylcyclopropanecarbonyl chloride

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Reaction Steps

1.0 g (0.0035 mol) of (±)-trans-3-(Z-2-chloro-2-(4-chloro-phenyl)-vinyl)-2,2-dimethyl-cyclopropanecarboxylic acid were dissolved in 20 ml of carbon tetrachloride, and 5 ml of thionyl chloride were added dropwise slowly at 25° C., while stirring. The mixture was then heated to the reflux temperature for 4 hours. After this reaction time, excess thionyl chloride and carbon tetrachloride were distilled off under a waterpump vacuum. Last residues of solvent were removed by brief incipient distillation at a bath temperature of 60° C./2 mm Hg. 1.03 g (96.9% of theory) of (±)-trans-3-(Z-2-chloro-2-(4-chloro-phenyl)-vinyl)-2,2-dimethyl-cyclopropanecarboxylic acid chloride were obtained as an oily liquid. ##STR21##

Provenance & Evidence