Nitrogen → HCID 23374575, compound

Participants

Reaction Steps

To a N2 covered, mechanically stirred solution of 4.93 ml (42.6 mmol) of phenylacetonitrile in 85 ml of CH2Cl2 was added 4.94 ml (46.9 mmol) of cis-1,4 dichloro-2-butene followed by 0.86 g (2.1 mmol) of Aliquat 336. There was then added 5.3 g (85.3 mmol) of powdered KOH in portions over 2.25 hours. A cold water bath was used to control a slight exotherm and keep the reaction temperature at about 25° C. during the addition. The reaction was stirred at room temperature for 1 hour and then heated in an oil bath at 55°-60° C. (reflux) for 1 hour. After allowing the reaction to cool, there was added 42 ml of H2O dropwise over 6 minutes. The mixture was transferred to a separatory funnel and mixed well. The aqueous fraction was separated and washed with Et2O. The combined organic fractions were dried over MgSO4 and concentrated in vacuo. The residue was distilled under reduced pressure and a single fraction was collected, 5.39 g, b.p. 62°-86° C. (0.05 mm Hg). This fraction was combined with 4.77 g of material from a previous run and heated neat under N2 in an oil bath at 200° C. for 30 minutes and then allowed to cool. The residue was chromatographed in two portions over silica gel (1% EtOAc: hexane) to yield 6.0 g of 4-Cyano-4-phenylcyclopentene.

Provenance & Evidence