4-Chlorobenzyl cyanide → HCID 21509099, compound

HRID 268469Notes

Reaction equation

HRID 268469 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:16]#[N:17])[C:9](=[O:15])[C:10]([O:12]CC)=O)=[CH:4][CH:3]=1.[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][C:26]#[N:27])=[CH:21][CH:20]=1.[O-]CC.[Na+].[Na]>O.C(O)(=O)C>[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([CH:25]([C:10](=[O:12])[C:9](=[O:15])[CH:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[C:16]#[N:17])[C:26]#[N:27])=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 2415824-Chlorobenzyl cyanideHCID 359722HCID 359722, compoundHCID 2723922Sodium ethoxideHCID 5360545Sodium

Product 1

HCID 21509099HCID 21509099, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Ethyl 3-(p-chlorophenyl)-3-cyanopyruvate (40 g., 0.16 mol.) and 49.8 g. (0.33 mol.) of p-chlorophenylacetonitrile were added to an alcoholic solution of sodium ethoxide [prepared from 7.36 g. (0.32 g.-atom) of sodium and 190 ml. of absolute ethanol] and the resulting solution was refluxed for two hours. The reaction mixture was diluted with water, acidified with acetic acid and cooled (ice bath) to yield 2,5-di-(p-chlorophenyl)-3,4-dioxoadiponitrile, m.p. 280°.

Workup

  1. temperaturethe resulting solution was refluxed for two hours
  2. temperaturecooled (ice bath)

Sources & evidence

ORD record
ord-d4e52c0e2db043ecbfb1798e1be42e64
Source dataset
uspto-grants-1976_03
Patent number
US03947580

Reaction notes

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