Hydrochloric Acid → 3-(2-Ethoxyethoxy)propanenitrile

HRID 557982Notes

Reaction equation

HRID 557982 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][OH:6])[CH3:2].[C:7](#[N:10])[CH:8]=[CH2:9].Cl>CO>[CH2:1]([O:3][CH2:4][CH2:5][O:6][CH2:9][CH2:8][C:7]#[N:10])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7855AcrylonitrileHCID 8076Glycol monoethyl ether

Product 1

HCID 205045543-(2-Ethoxyethoxy)propanenitrileYield 75.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To an ice-water cooled mixture of 2-ethoxyethanol (1 g, 11.1 mmol) and Triton B (40% in MeOH, 0.138 g, 0.33 mmol) was added acrylonitrile (0.618 g, 11.6 mmol) and the mixture was stirred at room temperature for 24 hours. It was then neutralized with 0.1 M HCl (3.3 cm3) and extracted with CH2Cl2 (2×10 cm3) The extracts were concentrated under reduced pressure and the residue was Kugelrohr-distilled to give the product 3-(2-ethoxyethoxy)propanenitrile (1.20 g, 75.5%) as a colorless oil, bp 100-130° C./20 Torr.

Workup

  1. extractionextracted with CH2Cl2 (2×10 cm3) The extracts
  2. concentrationwere concentrated under reduced pressure
  3. distillationthe residue was Kugelrohr-distilled

Sources & evidence

ORD record
ord-b2b4cad208c24821b58e1eaa5c9f4808
Source dataset
uspto-grants-2011_11
Patent number
US08062429B2

Reaction notes

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