Acrylonitrile → 3-(4-Methoxyphenoxy)propanenitrile

Participants

Reaction Conditions

Reaction Steps

A 740 g (5.96 mol, 1 eq.) sample of 4-methoxyphenol was charged to a 3 necked 5 L flask under nitrogen. Triton B (50 mL of a 30% wt. solution in methanol) was charged to the flask, and stirring initiated via an overhead stirrer. Acrylonitrile (2365 mL, 35.76 mol, 6 eq.) was then charged to the reaction flask in a single portion, and the reaction mixture heated at 78° C. for 36 h. HPLC analysis indicated that the reaction was complete at this point. Solvents were removed via rotary evaporation, and the resulting oil was chased with toluene to remove excess acrylonitrile. The crude material was recrystallized from TBME (tert-butyl methyl ether) 10 volumes relative to the crude weight), and dried in a vacuum oven to give 945 g of 3-(4-methoxyphenoxy)propionitrile as white crystals (Yield: 89.48%). 1H NMR (450 MHz, CDCl3): δ=2.72 (t, 2H; CH2CN); δ=3.83 (s, 3H; OCH3); δ=4.05 (t, 2H; OCH2); δ=6.70 (m, 4H; Ar—H); 13C NMR (112.5 MHz, CDCl3): d=18.843 (CH2CN); 55.902 (OCH3); 63.699 (OCH2); 114.947 (CH3OCCH); 116.183 (CH2OCCH); 117.716 (CN); 151.983 (CH3OC); 154.775 (CH2OC).

Provenance & Evidence