Hydracrylonitrile → 2-Cyanoethyl prop-2-ynoate

HRID 434330Notes

Reaction equation

HRID 434330 reaction equation
[C:1]([OH:5])(=[O:4])[C:2]#[CH:3].[C:6](#[N:10])[CH2:7][CH2:8]O>C1(C)C=CC(S(O)(=O)=O)=CC=1.C(Cl)(Cl)Cl>[C:1]([O:5][CH2:8][CH2:7][C:6]#[N:10])(=[O:4])[C:2]#[CH:3]

Participants

5

Reactant 2

HCID 8011HydracrylonitrileHCID 10110Propiolic Acid

Product 1

HCID 204932242-Cyanoethyl prop-2-ynoateYield 29%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 6212ChloroformSolvent

Procedure

A solution of 98 g of propiolic acid (1.4 moles), 99.5 g of hydracrylonitrile (1.4 moles), 2 g of p-toluenesulfonic acid and 200 ml of chloroform were refluxed, using a Soxhlet extractor filled with 3A molecular sieves to remove the water generated during the esterification. A total reflux time of 94 hours was employed. The reaction was cooled, poured into water and extracted with chloroform. The combined extracts were washed with dilute bicarbonate solution, dried (MgSO4), and concentrated to give 49.2 g (29 percent) of a liquid used without purification.

Workup

  1. customto remove the water
  2. customA total reflux time of 94 hours
  3. temperatureThe reaction was cooled
  4. additionpoured into water
  5. extractionextracted with chloroform
  6. washThe combined extracts were washed with dilute bicarbonate solution
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-fd0f65aeb5bf4d338462a705d92ef606
Source dataset
uspto-grants-1983_08
Patent number
US04396546

Reaction notes

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