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Solvent free imine formation: condensation of o-vanillin and methyl 4-aminobenzoate; methyl (E)-4-((2-hydroxy-3-methoxybenzylidene)amino)benzoate

SyntheticPage 819
DOI: 10.1039/SP819
Submitted Jun 13, 2017, published Jun 21, 2017
Steven M. Kennedy (Steven.Kennedy@millersville.edu), Kayla M. Rafferty (kmraffer@millersville.edu), Samantha K. Gillis (skgillis@millersville.edu)
A contribution from Kennedy Group, Millersville University


			Reaction Scheme: <img src="/images/empty.gif" alt="" />Solvent free imine formation<img src="/images/empty.gif" alt="" /><img src="/images/empty.gif" alt="" />:&nbsp;condensation of&nbsp;<em>o</em>-vanillin and methyl 4-aminobenzoate

Chemicals Used

o-Vanillin (99%, TCI America)
Methyl 4-Aminobenzoate (98%, TCI America)

Procedure

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%).

Author's Comments

For best results, mixing must continue until a dry redish-orange powder is produced.

Data

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).

13
C 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

Lead Reference

K.M. Touchette, J. Chem. Ed. 2006, 83 (6), 926. DOI: 10.1021/ed083p929

Supplementary Information

13C_NMR_Full_methyl (E)-4-((2- (CNMR_Full_methyl (E)-4-((2-hydroxy-3-methoxybenzylidene)amino)benzoate.pdf)
13C_NMR_Zoom_methyl (E)-4-((2- (CNMR_Zoommethyl (E)-4-((2-hydroxy-3-methoxybenzylidene)amino)benzoate.pdf)
1H_NMR_Full_methyl (E)-4-((2-h (HNMR_Fullmethyl (E)-4-((2-hydroxy-3-methoxybenzylidene)amino)benzoate.pdf)
1H_NMR_Zoom_methyl (E)-4-((2-h (HNMR_Zoom1.pdf)
Small Orange Crystals of methy (SmallOrangeCrystals_methyl (E)-4-((2-hydroxy-3-methoxybenzylidene)amino)benzoate_IMG.jpeg)

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Get structure file (.cdx, .sk2, .mol)

Keywords: aldehydes, amines, imine formation

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