SyntheticPage 819
DOI:
10.1039/SP819
Submitted Jun 13, 2017, published Jun 21, 2017
o-Vanillin (99%, TCI America)
Methyl 4-Aminobenzoate (98%, TCI America)
In a tared 250 mL beaker, o-vanillin (0.76 g, 5.0 mmol) and methyl 4-Aminobenzoate (0.76 g, 5.0 mmol) were vigorously mixed (using a glass-stirring rod) for 30 min to obtain a redish-orange homogenous dry powder; recrystallization from a mixture of 1:3 ethyl acetate:hexanes provided redish-orange crystals of methyl (E)-4-((2-hydroxy-3-methoxybenzylidene)amino)benzoate (1.23 g, 0.43 mmol, 86%).
For best results, mixing must continue until a dry redish-orange powder is produced.
1H NMR (400 MHz, CDCl3): δ 13.30, (s, 1H), 8.62 (s, 1H), 8.09 (d, 2H), 7.29 (d, 2H), 7.02 (t, 2H), 6.89 (t, 1H), 3.92 (ovr, 6H).
13C NMR (100 MHz, CDCl3): δ 166.51, 164.18, 152.13, 151.45, 148.45, 131.02, 128.36, 124.05, 121.17, 118.85, 118.80, 115.22, 56.16, 52.18.
IR (cm–1): ν 3675, 2988, 2902, 1719, 1077.
Rf 0.60 on SiO2 in 1:4 ethyl acetate:hexane
M.p. 134.6°C-135.3°C
K.M. Touchette, J. Chem. Ed. 2006, 83 (6), 926. DOI: 10.1021/ed083p929
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