Hydracrylonitrile → 2-Cyanoethyl prop-2-ynoate
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
Product 1
Reagents, catalysts & solvents 2
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 3 A 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
- additionfilled with 3 A molecular sieves
- customto remove the water
- customA total reflux time of 94 hours
- temperatureThe reaction was cooled
- additionpoured into water
- extractionextracted with chloroform
- washThe combined extracts were washed with dilute bicarbonate solution
- dry with materialdried (MgSO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-4a87bb4296684e359b17c6a0c3e00635
- Source dataset
- uspto-grants-1982_08
- Patent number
- US04346161
Reaction notes
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