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29 March 2004

(Z)-3-(2-Nitrophenyl)-2-(4-methylphenyl)acrylonitrile

Chemistry Department, Faculty of Science, King Abdul-Aziz University, Jeddah 21589, P.O. Box 80203, Saudi Arabia
Molbank 2004 m392 i001
(2Z)-3-(2-Nitrophenyl)-2-(4-methylphenyl)acrylonitrile (3) was prepared by Knoevenagel condensation of 2-nitrobenzaldehyde 1 and 4-methylphenylacetonitrile 2 in ethanol using KOH as a base [,]. 2-Nitrobenzaldehyde 1 (3.01 g, 0.02 mol) and 4-methylphenylacetonitrile 2 (3.32 g, 0.02 mol ) in ethanol (35 mL) were heated under reflux for seven minutes. Potassium hydroxide (1.12 g, 0.02 mol) was added in one portion and the reflux was continued for two hours. The reaction mixture was cooled to room temperature and the solid formed was filtered, washed with water and finally with ethanol (2 x 30 mL) and dried. The product was recrystallized from ethanol as yellow crystals (2.63g, 95%).
M.p. 142-144 ºC.
UV lmax (nm; EtOH)/e (dm3.mol-1.cm-1) 350/15500.
IR (cm-1; KBr Disk) 2215 (CN), 1606 (C=C).
1H-NMR (400 MHz; CDCl3, Me4Si, dH): 8.24 (1H, d, J= 9.4 Hz), 8.00 (1H, s, CH=C ), 7.94 (1H, d, J = 7.7 Hz), 7.77 (1H, d), 7.64 ( 1H, dd), 7.60 (2H,d, 8.1 Hz), 7.28 ( 2H, d, 8.2 Hz), 2.38 (3H, s, MePh).
13C-NMR (100 MHz; CDCl3, Me4Si, dC): 21.2, 108.6, 110.5, 110.8, 118.8, 124.2, 125.6, 126.8, 129.7, 131.9, 138.9, 141.1, 148.9 and 150.9.
Elemental Analysis: Calculated for C16H12N2O2 (264.26): C 72.72, H 4.58, N 10.60; Found: C 72.61, H 4.76, N 10.45.

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

References

  1. Jones, G. Org. React. 1967, 15, 204–599.
  2. Stewart, J. T.; Kim, M. J. Chem. Eng. Data 1987, 32, 387–389.

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