Sodium Cyanide → 2-Chloro-6-methoxybenzeneacetonitrile

HRID 495514Notes

Reaction equation

HRID 495514 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH3:11])[C:3]=1[CH2:4]Br.[C-:12]#[N:13].[Na+]>C1(C)C=CC=CC=1.O.CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-]>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH3:11])[C:3]=1[CH2:4][C:12]#[N:13]

Participants

6

Reactant 2

HCID 8929Sodium CyanideHCID 223274432-(Bromomethyl)-1-chloro-3-methoxybenzene

Product 1

HCID 223275112-Chloro-6-methoxybenzeneacetonitrileYield 87.3%

Reagents, catalysts & solvents 3

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

483 g of 2-chloro-6-methoxybenzyl bromide in 410 ml of toluene are reacted with 131 g of sodium cyanide in 132 ml of water and 3.28 g of Aliquat 336. 325 g of colorless oil are obtained (b.p. 103° C./0.08 mbar).

Sources & evidence

ORD record
ord-a16bc99982ed4c099aa533afc6969057
Source dataset
uspto-grants-2005_09
Patent number
US06939888B2

Reaction notes

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