Phenylacetonitrile → Ethyl 3-cyano-3-phenylpyruvate

HRID 1287534Notes

Reaction equation

HRID 1287534 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 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 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 2 hours
  3. temperatureAfter cooling
  4. additiondiluting with 2500 ml
  5. extractionof water and extracting with ether
  6. customThe solid was removed
  7. washwashed with water

Sources & evidence

ORD record
ord-bb96c687981f40c59b4051c543d2119d
Source dataset
uspto-grants-1976_10
Patent number
US03984559

Reaction notes

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