Phenylacetonitrile → 3,4-Dioxo-2,5-diphenylhexanedinitrile

HRID 1287529

Reaction equation

HRID 1287529 reaction equation
[C:1]([CH:3]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:4](=[O:10])[C:5]([O:7]CC)=O)#[N:2].[C:17]1([CH2:23][C:24]#[N:25])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[O-]CC.[Na+].[Na]>C(O)(=O)C.O>[C:17]1([CH:23]([C:5](=[O:7])[C:4](=[O:10])[CH:3]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:1]#[N:2])[C:24]#[N:25])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 8794PhenylacetonitrileHCID 22845Ethyl 3-cyano-3-phenylpyruvateHCID 2723922Sodium ethoxideHCID 5360545Sodium

Product 1

HCID 252993,4-Dioxo-2,5-diphenylhexanedinitrile

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Ethyl 3-cyano-3-phenylpyruvate (50.0 g., 0.23 mol.) and 41.0 g. (0.35 mol.) of phenylacetonitrile were added to an alcoholic solution of sodium ethoxide [prepared from 13.4 g. (0.58 g.-atom) of sodium and 360 ml. of absolute ethanol] and the resulting yellow solution was refluxed for 1.75 hours. The cooled solution was diluted with 700 ml. of water and acidified by slow addition of acetic acid. After further cooling in ice, the suspension was filtered and the solid was washed with water and dried to give 2,5-diphenyl-3,4-dioxoadiponitrile, m.p. 284°-286° dec.

Workup

  1. temperaturethe resulting yellow solution was refluxed for 1.75 hours
  2. additionThe cooled solution was diluted with 700 ml
  3. temperatureAfter further cooling in ice
  4. filtrationthe suspension was filtered
  5. washthe solid was washed with water
  6. customdried

Sources & evidence

ORD record
ord-fc87dec1d50c4f6dae342e7b690a297e
Source dataset
uspto-grants-1976_10
Patent number
US03984559

Linked notes

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