Phenylacetonitrile → Ethyl 3-cyano-3-phenylpyruvate

HRID 267754

Reaction equation

HRID 267754 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+]>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

5

Reactant 3

HCID 8794PhenylacetonitrileHCID 2723922Sodium ethoxideHCID 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. (1.0m.) of phenylacetonitrile and 326 ml. (2.4m.) of ethyl oxalate is added to an ethanol solution of sodium ethoxide (prepared by dissolving 23.8 g., 1.08m. of sodium in 500 ml. of absolute ethanol) and refluxed two hours. After cooling, diluting with 2500 ml. of water and extracting with ether, the solution is acidified with acetic acid. The solid is removed and washed with water to give ethyl 3-cyano-3-phenylpyruvate, m.p. 127°-129° C.

Workup

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

Sources & evidence

ORD record
ord-5a583588cf9a4ecd87ac26e99fc1ed56
Source dataset
uspto-grants-1976_03
Patent number
US03944571

Linked notes

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