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Solvent free imine formation: condensation of o-vanillin and 3,4-dimethylaniline; (E)-2-(((3,4-dimethylphenyl)imino)methyl)-6-methoxyphenol

SyntheticPage 821
DOI: 10.1039/SP821
Submitted Jun 14, 2017, published Jun 21, 2017
Steven M. Kennedy (Steven.Kennedy@millersville.edu), Christa M. Gonzales (cmgonza1@millersville.edu), Huy T. Nguyen (htnguyen@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="" />:&nbsp;condensation of&nbsp;<em>o</em>-vanillin and 3,4-dimethylaniline

Chemicals Used

o-Vanillin (99%, TCI America)
3,4-Dimethylaniline (99%, TCI America)

Procedure

In a tared 250 mL beaker, o-vanillin (0.76 g, 5.0 mmol) and 3,4-dimethylaniline (0.61 g, 5.0 mmol) were were vigorously mixed (using a glass-stirring rod) for 30 min to obtain a bright orange homogenous dry powder; recrystallization from hexanes provided orange crystals of (E)-2-methoxy-6-((p-tolylimino)methyl)phenol (1.19 g, 4.8 mmol, 93% yield).

Author's Comments

This compound was slow (~20 min) to become a solid.

Data

1H NMR (400 MHz, CDCl3): δ 13.90 (s, 1H, ArOH), 8.59 (s, 1H, N=CH), 7.15 (d, 1H), 7.07-6.95 (m, 4H), 6.85 (t, 1H), 3.92 (s, 3H, ArOCH3), 2.29 (s, 3H, ArCH3), 2.26 (s, 3H, ArCH3).

13C NMR (100 MHz, CDCl3): δ  161.38, 151.43, 148.41, 145.69, 137.71, 135.68, 130.45, 123.57, 122.36, 119.14, 118.35, 118.25, 114.33, 56.10, 19.88, 19.40.

Lead Reference

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

Other References

A. Senier, F.G. Shepheard, R. Clarke, Journal of the Chemical Society, Tran. 1912, 101, 1950.

Supplementary Information

13C_NMR_Full_(E)-2-(((3,4-dime (CG_CNMR_Full.pdf)
13C_NMR_Zoom_(E)-2-(((3,4-dime (CG_CNMR_Zoom.pdf)
1H_NMR_Full_(E)-2-(((3,4-dimet (CG_HNMR_Full.pdf)
1H_NMR_Zoom_(E)-2-(((3,4-dimet (CG_HNMR_Zoom.pdf)
Orange Crystals of (E)-2-(((3, (IMG_3209.jpg)

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

Keywords: aldehydes, amines, imine formation