Diethyl Oxalate → Ethyl 3-cyano-2-oxo-3-p-tolylpropanoate

HRID 267759

Reaction equation

HRID 267759 reaction equation
[CH3:1][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+]>[C:9]([CH:8]([C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=1)[C:11](=[O:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13])#[N:10]

Participants

4

Reactant 2

HCID 7268Diethyl OxalateHCID 76280p-Tolylacetonitrile

Product 1

HCID 11481648Ethyl 3-cyano-2-oxo-3-p-tolylpropanoate

Reagents, catalysts & solvents 1

HCID 2723922Sodium ethoxideSolvent

Procedure

Following the procedures outlined in Examples 1 and 3, p-methylphenylacetonitrile and diethyl oxalate are reacted in alcoholic sodium ethoxide to obtain ethyl 3-cyano-3-(p-methylphenyl)-pyruvate, m.p. 86°-88° C. The latter is reacted with p-methylphenylacetonitrile to give 2,5-di-(p-methylphenyl)-3,4-dioxoadiponitrile, m.p. 270°-272° C.

Sources & evidence

ORD record
ord-93cc3abd2e374ecbb2212d05d7bf761a
Source dataset
uspto-grants-1976_03
Patent number
US03944571

Linked notes

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