Toluene → HCID 178444317, compound

Participants

Reaction Steps

A solution of methylmagnesium iodide in diethyl ether (prepared from 384 mg of magnesium shavings and 0.984 ml of methyl iodide in 30 ml of diethyl ether) was treated dropwise at room temperature with a solution of 2.0 g of p-[trans-4-(trans-1-pentenyl)cyclohexyl]benzonitrile. The mixture was heated to reflux for 15 minutes. 30 ml of toluene were subsequently added to the mixture, the diethyl ether was distilled off and the resulting mixture was heated to reflux for a further 1.5 hours. The mixture was then treated cautiously at 0° C. with saturated ammonium chloride solution and partitioned three times in diethyl ether/water. The organic extracts were washed twice with water, dried over magnesium sulphate, filtered and evaporated. Chromatographic separation of the yellow, crystalline residue (2.6 g) on silica gel with ethyl acetate/petroleum ether (vol. 5:95) gave 1.85 g (87%) of p-[trans-4-(trans-1-pentenyl)cyclohexyl]acetophenone as light yellow crystals.

Provenance & Evidence