Water → HCID 86738077, compound

Participants

Reaction Steps

3.4 g (0.0112 mole) of (+)-trans-Z-3-(2-chloro-2-(4-chloro-phenyl)-vinyl)-2,2-dimethyl-1-cyclopropanecarboxylic acid chloride, dissolved in 10 ml of cyclohexane, were added dropwise to a mixture of 50 ml of cyclohexane, 0.87 g of sodium cyanide, 1.3 ml of water, 2.42 g (0.0112 mole) of 3-phenoxy-4-fluorobenzaldehyde and 0.2 g of tetrabutylammonium bromide at 20°-25° C., whilst stirring, and the mixture was then stirred at 20°-25° C. for 4 hours. 100 ml of toluene were then added to the reaction mixture and the mixture was extracted twice by shaking with 60 ml of water each time. The organic phase was separated off and dried over magnesium sulphate and the solvent was distilled off under a waterpump vacuum. Last residues of solvent were removed by brief incipient distillation at a bath temperature of 60° C./1 mm Hg. 4.4 g (77% of theory) of (+)-trans-Z-3-(2-chloro-2-(4-chloro-phenyl)vinyl)-2,2-dimethyl-cyclopropane-carboxylic acid (±)-α-cyano-3-phenoxy-4-fluoro-benzyl ester were obtained as a viscous oil with an optical rotation [α]D of +58.2° (C=100 mg in 10 ml of CHCl3).

Provenance & Evidence