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

HRID 2403107Notes

Reaction equation

HRID 2403107 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 0.1M 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 coloured oil, by 150-170° C./20 Torr.

Workup

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

Sources & evidence

ORD record
ord-a2a91f463db44936b7d1ca60f5b376a6
Source dataset
uspto-grants-2014_08
Patent number
US08802609B2

Reaction notes

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