Acrylonitrile → 65195-19-9

Participants

Reaction Conditions

Reaction Steps

Compound 18 was prepared by modification of a reported procedure by Lynn (U.S. Pat. No. 2,975,187). To a vigorously stirred mixture of 2-oxazolidinone (87 g, 1 mol), 50% sodium hydroxide (w/w, 4 g) and toluene (250 mL) maintained at 55°-60° C., acrylonitrile (106 g, 2 mol) was added dropwise over a period of 30 min. The mixture was then stirred at 80° C. for 1 h and refluxed for 3 h. Additional acrylonitrile (50 mL) was added towards the end of the reaction to drive it to completion. Excess acrylonitrile was removed by distillation, and the residue was left at room temperature overnight. The mixture was filtered, cooled in an ice bath and acidified with concentrated H2SO4 to ~ pH 1. The salt was removed by filtration, and the filtrate was dried over anhydrous MgSO4. The residue obtained after removal of the solvent under vacuum was dried under high vacuum overnight to give 117 g (84%) of 18 as a colorless oil: 1H NMR (CDCl3) δ 2.68 (t, 2, CH2CH2CN), 3.57 (t, 2, NCH2CH 2), 3.75 (t, 2, NCH2CH2O) and 4.39 (t, 2, CH2H2O--).

Provenance & Evidence