Phenylacetonitrile → HCID 13642035, compound

Participants

Reaction Steps

384 g (4.8 mol) of 50% sodium hydroxide and 12 g of hexadecyl-trimethylammonium bromide are placed in a 2-liter flask provided with a thermometer, stirrer and reflux condenser and there is added dropwise while stirring within 0.25 hour a mixture of 469 g of benzyl cyanide (4 mol) and 502 g (4.8 mol) of prenyl chloride(1). During the addition the mixture warms and it is subsequently stirred for a further 3 hours at 60° C. After cooling, the mixture is poured on to 500 g of ice, extracted four times with ether and washed neutral with water. The phase separation can be facilitated by the addition of a small amount of alcohol. After drying over sodium sulphate, the ether is evaporated and the residue is fractionally distilled. There are obtained 444 g of 5-methyl-2-phenyl-4-hexene nitrile of boiling point 108°-109° C./3 mmHg; nD20 =1.5171-72; yield 60%.

Provenance & Evidence