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

HRID 267755

Reaction equation

HRID 267755 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.CC[O-].[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 m.) and 41.0 g. (0.35 m.) of phenylacetonitrile are added to an alcoholic solution of sodium ethylate [prepared from 13.4 g. (0.58 g. atom) of sodium and 360 ml. of absolute ehtanol] and the resulting yellow solution is refluxed for one and three-quarter hours. The cooled solution is diluted with 700 ml. of water and acidified by slow addition of acetic acid. After further cooling in ice, the suspension is filtered and the removed solid washed with water and dried to give 2,5-diphenyl-3,4-dioxoadiponitrile, m.p. 284°-286° C. (d.).

Workup

  1. temperaturethe resulting yellow solution is refluxed for one and three-quarter hours
  2. additionThe cooled solution is diluted with 700 ml
  3. temperatureAfter further cooling in ice
  4. filtrationthe suspension is filtered
  5. washthe removed solid washed with water
  6. customdried

Sources & evidence

ORD record
ord-38a1144efef546908942114f40e3b1dc
Source dataset
uspto-grants-1976_03
Patent number
US03944571

Linked notes

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