Sodium Methoxide → Ethyl cyanoacrylate

HRID 279789

Reaction equation

HRID 279789 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH:5]([C:15]#[N:16])[CH2:6]C(C#N)C(OCC)=O)[CH3:2].C[O-].[Na+].C(OC(=O)CCCC(OC#N)=O)#N>CO.O>[CH2:1]([O:3][C:4](=[O:17])[C:5]([C:15]#[N:16])=[CH2:6])[CH3:2]

Participants

7

Reactant 4

HCID 10942334Sodium Methoxide2×HCID 15932776Diethyl 2,4-dicyanopentanedioateHCID 86740765DicyanoglutarateHCID 178486302HCID 178486302, compound

Product 1

HCID 81530Ethyl cyanoacrylateYield 59.6%

Reagents, catalysts & solvents 2

HCID 887MethanolCatalystHCID 962WaterSolvent

Procedure

494.0 g (2.074 moles) of 2,4-dicyanoglutaric acid diethyl ester were reacted in the absence of water with 44.8 g of polyoxymethylene (92%; 1.372 moles) and 3 g of a 30% solution of sodium methylate in methanol (0.0167 mole). The quantity of sodium methylate used corresponded to an excess of 1.25 millimoles per mole of dicyanoglutarate. The reaction was carried out over a period of 45 minutes at a temperature of 100° C.-130° C. The water present was then removed using an oil pump vacuum. Thermolysis produced 154.5 g (1.236 moles) of 2-cyanoacrylic acid ethyl ester after distillation. The yield thus amounted to 31.3% by weight, based on 2,4-dicyanoglutarate.

Workup

  1. customThe water present was then removed

Sources & evidence

ORD record
ord-ac7b614eb6fb42a09e49033fdddffcb0
Source dataset
uspto-grants-1986_05
Patent number
US04587059

Linked notes

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