Hydrochloric Acid → Diethyl bis(2-cyanoethyl)propanedioate

HRID 653803Notes

Reaction equation

HRID 653803 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].CO.[C:14](#[N:17])[CH:15]=[CH2:16].Cl>O1CCOCC1>[C:14]([CH2:15][CH2:16][C:2]([CH2:16][CH2:15][C:14]#[N:17])([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][CH2:10][CH3:11])=[O:8])#[N:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 7761Diethyl MalonateHCID 7855Acrylonitrile

Product 1

HCID 74046Diethyl bis(2-cyanoethyl)propanedioateYield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of diethyl malonate (81 g) in 100 g of 1,4-dioxane containing Triton B (10g of 40% methanol solution) was added dropwise acrylonitrile (55 g) in a period of 30 minutes. The reaction is highly exothermic, and the temperature was controlled at 30°-40° C. by means of a water bath. The reaction mixture was stirred overnight, and later poured into 600 ml of ice-water containing hydrochloric acid (5 ml of conc. HCl). The white precipitate formed was collected by filtration and washed with water. The crude product (m.p. 61°-63° C., 100% yield) was used for the next step without further purification.

Workup

  1. customthe temperature was controlled at 30°-40° C. by means of a water bath
  2. customThe white precipitate formed
  3. filtrationwas collected by filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-63bc150a7e1246b482d7e6feac6265f4
Source dataset
uspto-grants-1992_07
Patent number
US05128466

Reaction notes

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