Ethylene Glycol → 3,3'-(Ethylenedioxy)dipropiononitrile

HRID 557986Notes

Reaction equation

HRID 557986 reaction equation
[CH2:1]([OH:4])[CH2:2][OH:3].[C:5](#[N:8])[CH:6]=[CH2:7].Cl>CO>[CH2:1]([O:4][CH2:7][CH2:6][C:5]#[N:8])[CH2:2][O:3][CH2:7][CH2:6][C:5]#[N:8]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 313Hydrochloric AcidHCID 7855Acrylonitrile

Product 1

HCID 769213,3'-(Ethylenedioxy)dipropiononitrileYield 39.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Small scale: Ethylene glycol (1 g, 16.1 mmol) was mixed with Triton B (40% in MeOH, 0.22 g, 0.53 mmol) and cooled in an ice-bath while acrylonitrile (1.71 g, 32.2 mmol) was added. The mixture was stirred at room temperature for 60 hours after which it was neutralized with 0.1 M HCl (0.6 cm3) and extracted with CH2Cl2 (80 cm3) The extracts were concentrated under reduced pressure and the residue was Kugelrohr-distilled to give 3,3′-(ethane-1,2-diylbis(oxy))dipropanenitrile (1.08 g, 39.9%) as a light colored oil, bp 150-170° C./20 Torr.

Workup

  1. additionwas added
  2. extractionextracted with CH2Cl2 (80 cm3) The extracts
  3. concentrationwere concentrated under reduced pressure
  4. distillationthe residue was Kugelrohr-distilled

Sources & evidence

ORD record
ord-e70fedd02b1a43f6afcc8353ddc14dbc
Source dataset
uspto-grants-2011_11
Patent number
US08062429B2

Reaction notes

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