Chloroform → HCID 13108922, compound

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Reaction Steps

Ethyl 2-(2-naphthyl)-acrylate (3.86 g) was dissolved in chloroform (4.3 g) tetraethylbenzyl ammonium chloride (36 mg) was added and sodium hydroxide (9 ml; 50%) added dropwise over 10 minutes at room temperature. The reaction mixture was stirred for an additional 2 hours and then quenched in ice water and extracted with ether. The solvent layer was washed sequentially with water, dilute hydrachloric acid and water again, and dried over anhydrous sodium sulphate. After evaporation of the solvents, the oily residue was chromatographed on silica gel using petroleum ether(b.p. 60°-80°) methylene chloride as eluent. The main fraction, a yellow oil (4.85 g), was distilled under vacuum to yield the ethyl ester of 2,2-dichloro 1-(2-naphthyl)cyclopropanecarboxylic acid identified by its i.r. and p.m.r. spectra. This ester was hydrolysed by refluxing in a 1 N sodium hydroxide/ethanol solution. On acidification thecyclopropane acid was obtained as a solid. This was recrystallised from petroleum ether (b.p. 40°-60°)/methylene chloride to yield (0.97 g; 31%) of the acid, m.p. 154°-5° C.

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