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

HRID 1906314Notes

Reaction equation

[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][C:7]#[N:8])=[CH:4][CH:3]=1.[OH-].[Na+].[CH:13](Br)([CH3:15])[CH3:14].CCOCC>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([CH:6]([C:7]#[N:8])[CH:13]([CH3:15])[CH3:14])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 40 °C

Procedure

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.

Workup

temperaturewith reflux condenser
temperatureinitially by cooling
temperaturelater by heating
temperatureThe reaction mixture is cooled to room temperature
customthe aqueous phase is separated off
washthe organic phase is washed successively with 5% strength hydrochloric acid, sodium bicarbonate solution and water
dry with materialAfter having been dried with sodium sufate
customthe solvent is removed by distillation

Sources & evidence

ORD record: ord-9c904127256c496f893cf1be4f368f75
Source dataset: uspto-grants-1987_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04650910

Reaction notes

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