Diethyl Oxalate → HCID 359722, compound

HRID 268468Notes

Reaction equation

HRID 268468 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1.[C:11](OCC)(=[O:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13].[O-]CC.[Na+].[Na]>C(O)(=O)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:9]#[N:10])[C:11](=[O:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 7268Diethyl OxalateHCID 2415824-Chlorobenzyl cyanideHCID 2723922Sodium ethoxideHCID 5360545Sodium

Product 1

HCID 359722HCID 359722, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A mixture of 45.3 g. (0.31 mol.) of p-chlorophenyl-acetonitrile and 107 g. (0.72 mol., 99 ml.) of diethyl oxalate in an alcoholic sodium ethoxide solution [prepared by dissolving 7.13 g. (0.31 g.-atom) of sodium in 120 ml. of absolute ethanol] was refluxed with stirring for two hours. The cooled reaction mixture was diluted with 700 ml. of water, acidified with acetic acid and cooled to ice bath temperature. The resulting solid was collected and recrystallized from aqueous methanol to give ethyl 3 -(p-chlorophenyl)-3-cyanopyruvate, m.p. 134°-135°.

Workup

  1. additionA mixture of 45.3 g
  2. customThe cooled reaction mixture
  3. additionwas diluted with 700 ml
  4. temperaturecooled to ice bath temperature
  5. customThe resulting solid was collected
  6. customrecrystallized from aqueous methanol

Sources & evidence

ORD record
ord-e4110cadfd0044f88393a719eb35dfe9
Source dataset
uspto-grants-1976_03
Patent number
US03947580

Reaction notes

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