Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1906314Generated: October 31, 2026

Diethyl Ether → BENZENEACETONITRILE, 4-CHLORO-.ALPHA.-(1-METHYLE

https://huagongshe.com/reaction/1906314

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiethyl EtherHCID 3283—
Reactant2-BromopropaneHCID 6358—
ReactantSodium HydroxideHCID 14798—
Reactant4-Chlorobenzyl cyanideHCID 241582—
CatalystTetrabutylammonium BromideHCID 74236—
SolventWaterHCID 962—
ProductBENZENEACETONITRILE, 4-CHLORO-.ALPHA.-(1-METHYLEHCID 102734—

Reaction Conditions

Temperature40 °C

Reaction Steps

469 g (3.1 mol) of 4-chlorobenzyl cyanide, 30 g of tetrabutylammonium bromide, 1500 g of 50% strength sodium hydroxide solution and 438 g (3.56 mol) of isopropyl bromide are initially introduced into a 4 l multineck apparatus with reflux condenser and internal thermometer. The temperature rises after the stirrer is switched on. It is maintained at 40° C. for 4 h, initially by cooling and later by heating. The reaction mixture is cooled to room temperature, poured into a mixture of 500 ml of ether and 500 ml of water, the aqueous phase is separated off, and the organic phase is washed successively with 5% strength hydrochloric acid, sodium bicarbonate solution and water. After having been dried with sodium sufate, the solvent is removed by distillation. The residue remaining is 585.3 g of 97% pure 4-α-isopropylbenzyl cyanide. The product is pure enough for the subsequent hydrogenation.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS04650910
Source datasetuspto-grants-1987_03
ORD IDord-9c904127256c496f893cf1be4f368f75
Source noteuspto-grants-1987_03