Acrylonitrile → 3-(4-Methoxyphenoxy)propanenitrile

HRID 1873920Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.[C:10](#[N:13])[CH:11]=[CH2:12]>CO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:12][CH2:11][C:10]#[N:13])=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 78 °C

Procedure

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): δ=18.843 (CH2CN); 55.902 (OCH3); 63.699 (OCH2); 114.947 (CH3OCCH); 116.183 (CH2OCCH); 117.716 (CN); 151.983 (CH3OC); 154.775 (CH2OC).

Workup

custominitiated via an overhead stirrer
customSolvents were removed via rotary evaporation
customto remove excess acrylonitrile
customThe crude material was recrystallized from TBME (tert-butyl methyl ether) 10 volumes relative to the crude weight), and
customdried in a vacuum oven

Sources & evidence

ORD record: ord-65f224d85cdd43248f71df42f307c4be
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08304447B2

Reaction notes

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