SYNTHESIS OF 3-ETHOXYPROPIONITRILE

• Regenerate the resin [Zerolit FF or Amberlite (IRA-400)] by washing it on a Buchner funnel with 5 per cent sodium hydroxide solution (5-6 times the volume of the resin); rinse the resin with distilled water until the washings are neutral and dry in the air. 

• In a 500-ml three-necked flask equipped with a reflux condenser, stirrer and a dropping funnel, place 25g of the regenerated resin and 46 g (58.5 ml, 1 mol) of ethanol. Immerse the flask in an ice bath to control the subsequent initial exothermic reaction and to hold the temperature below 15-20°C throughout the experiment. 

• Add 67g (85 ml, 1.26 mol) of redistilled acrylonitrile slowly to the well stirred mixture in the flask over a period of 1-2 hours; continue the stirring for a further 1.5 hours. 

• Separate the resin by filtration. Distil the filtrate at atmospheric pressure to 100 °C in order to remove unreacted acrylonitrile and ethanol, and the residue under reduced pressure. 

• Collect the 3-ethoxy- propionitrile at 77-78 °C/25 mmHg. The yield is about HOg (90%); p.m.r spectrum (CCl₄ , TMS), 𝜹1.20 (t,3H), 2.50 (t,2H), 3.52 (t,2H) and 3.58 (q, 2H). 

• The last two signals overlap, but may be clearly discerned.