Toluene → 4-Chloro-2-methylbenzeneacetonitrile

HRID 993228Notes

Reaction equation

HRID 993228 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[C:4](OC)[CH:3]=1.[C-:12]#[N:13].[Na+].[C:15]1(C)C=CC=CC=1>O.CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-]>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][C:12]#[N:13])=[C:4]([CH3:15])[CH:3]=1

Participants

6

Reactant 3

HCID 1140TolueneHCID 8929Sodium CyanideHCID 223274741-(Bromomethyl)-4-chloro-2-methoxybenzene

Product 1

HCID 184099344-Chloro-2-methylbenzeneacetonitrile

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 962WaterSolvent

Procedure

269 g of 4-chloro-2-methoxybenzyl bromide in 214 ml of toluene are reacted with 68.2 g of sodium cyanide in 69 ml of water and 1.8 g of Aliquat 336. 141 g of colorless oil are obtained (b.p. 107° C./0.08 mbar).

Sources & evidence

ORD record
ord-8a7fba9245b44deb9fec596dd436d4de
Source dataset
uspto-grants-2002_10
Patent number
US06472419B1

Reaction notes

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