Heptane → HCID 86739665, compound

Participants

Reaction Steps

To a solution of 0.62 g (0.011 mole) of potassium hydroxide in 3.65 ml distilled water was added, with stirring, 1.8 g (0.0074 mole) of cis-3-(2-chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarboxylic acid and 14.6 ml of heptane. The reaction mixture was heated at reflux temperature, and the water was collected in a Dean-Stark trap. The anhydrous reaction mixture was then cooled, and 1.5 g (0.0069 mole) of 3-chloromethyl-2-methyl-[1,1'-biphenyl] and 14.6 ml of acetonitrile were added. The reaction mixture was stirred and heated at reflux temperature for 16 hours, then cooled and diluted with water. Diethyl ether was added and the two phases were separated. The aqueous phase was washed with heptane, then with diethyl ether. The organic phase and washings were combined, dried with anhydrous sodium sulfate and filtered. The solvents were removed from the filtrate under reduced pressure to give a yellow oil which was dissolved in methylene chloride and subjected to preparative liquid chromatography. A mixture of hexane and methylene chloride (2:1) was used as eluant. Appropriate fractions, as determined by thin layer and gas liquid phase chromatography, were combined to give 1.6 g of [2-methyl(1,1'-biphenyl)-3-yl]methyl cis-3-(2-chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarboxylate as a clear, colorless oil.

Provenance & Evidence