Hydrochloric Acid → Diethyl bis(2-cyanoethyl)propanedioate

HRID 557987Notes

Reaction equation

HRID 557987 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:12](#[N:15])[CH:13]=[CH2:14].Cl>CO.O1CCOCC1>[C:12]([CH2:13][CH2:14][C:2]([CH2:14][CH2:13][C:12]#[N:15])([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][CH2:10][CH3:11])=[O:8])#[N:15]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 7761Diethyl MalonateHCID 7855Acrylonitrile

Product 1

HCID 74046Diethyl bis(2-cyanoethyl)propanedioateYield 75.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of diethyl malonate (1 g, 6.2 mmol) and Triton B (40% in MeOH, 0.13 g, 0.31 mmol) in dioxane (1.2 cm3) was added dropwise acrylonitrile (0.658 g, 12.4 mmol) and the mixture was stirred at 60° C. overnight. The mixture was then cooled to room temperature and neutralized with 0.1 M HCl (3 cm3) and poured to ice-water (10 cm3). Crystals precipitated during 30 min. These were collected by filtration and recrystallised from EtOH (cooling in freezer before filtering off) to give diethyl 2,2-bis(2-cyanoethyl)malonate (1.25 g, 75.8%) as a white solid, mp 62.2-63.5° C.

Workup

  1. customCrystals precipitated during 30 min
  2. filtrationThese were collected by filtration
  3. customrecrystallised from EtOH (cooling in freezer before filtering off)

Sources & evidence

ORD record
ord-621a6a3abe4b4b0cbd4793fd07167772
Source dataset
uspto-grants-2011_11
Patent number
US08062429B2

Reaction notes

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