Phenylacetonitrile → Ethyl 3-cyano-3-phenylpyruvate

HRID 1579457Notes

Reaction equation

HRID 1579457 reaction equation
[C:1]1([CH2:7][C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:10]([O:15][CH2:16][CH3:17])(=[O:14])[C:11]([O-])=[O:12].[O-]CC.[Na+].[Na]>C(O)C>[C:8]([CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:11](=[O:12])[C:10]([O:15][CH2:16][CH3:17])=[O:14])#[N:9]

Participants

6

Reactant 4

HCID 8794PhenylacetonitrileHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 21943339Ethanedioic acid, monoethyl ester

Product 1

HCID 22845Ethyl 3-cyano-3-phenylpyruvate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 117.1 g. (1.0 mol.) of phenylacetonitrile and 326 ml. (2.4 mol.) of ethyl oxalate was added to an ethanol solution of sodium ethoxide [prepared by dissolving 23.8 g. (1.08 g.-atom) of sodium in 500 ml. of absolute ethanol] and refluxed for 2 hours. After cooling, diluting with 2500 ml. of water and extracting with ether, the solution was acidified with acetic acid. The solid was removed by filtration and washed with water to give ethyl 3-cyano-3-phenylpyruvate, m.p. 127°-129°.

Workup

  1. additionA mixture of 117.1 g
  2. temperaturerefluxed for 2 hours
  3. temperatureAfter cooling
  4. additiondiluting with 2500 ml
  5. extractionof water and extracting with ether
  6. customThe solid was removed by filtration
  7. washwashed with water

Sources & evidence

ORD record
ord-7f0ab090401e43569012ea94e59f536c
Source dataset
uspto-grants-1976_01
Patent number
US03931207

Reaction notes

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