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Volume 2010
Issue 2
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Short Note

3-Hydroxy-4-{[(4-chlorophenyl)imino]methyl}phenyl Octadecanoate

by
Sie-Tiong Ha
1,*,
Mei-Yoke Ng
2,
Teck-Ming Koh
2,† and
Teck-Leong Lee
1,2
1
Department of Chemical Science, Faculty of Science, Universiti Tunku Abdul Rahman, Jln Universiti, Bandar Barat, 31900 Kampar, Perak, Malaysia
2
Department of Science, Faculty of Engineering and Science, Universiti Tunku Abdul Rahman, Jln Genting Jelang, Setapak, 53300 Kuala Lumpur, Malaysia
*
Author to whom correspondence should be addressed.
†
Present address: Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543.
Molbank 2010, 2010(2), M674; https://doi.org/10.3390/M674
Submission received: 25 March 2010 / Accepted: 8 April 2010 / Published: 9 April 2010
Browse Figure
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Abstract

:
A new Schiff base ester, 3-hydroxy-4-{[(4-chlorophenyl)imino]methyl}phenyl octadecanoate, was synthesized and its IR, 1H NMR, 13C NMR and MS spectroscopic data are presented.

Graphical Abstract

Schiff bases have attracted overwhelming attentions from many researchers owing to their importance in exhibiting thermochromism and photochromism [1,2,3,4]. The presence of a long alkyl chain at the para position of the aldehyde or aniline fragment of N-benzylideneanilines has been regarded as one of the important elements which favours the existence of liquid crystal phases [5,6,7,8,9].

Synthesis

4-Formyl-3-hydroxyphenyl octadecanoate was previously prepared via Steglich esterification [10]. In a round-bottom flask, a mixture of the aldehyde I (1.74 g, 5.0 mmol), 4-chloroaniline (0.64 g, 5.0 mmol) and absolute ethanol (40 mL) was refluxed with stirring for 3 h. The reaction mixture was filtered and the solvent was removed from the filtrate by evaporation. Recrystallization from absolute ethanol gave the title compound as a yellow solid (0.87 g, 34%).
Molbank 2010 m674 i001
Melting point: 116.1 °C
MS (EI): m/z = 514 (M+)
IR (KBr, cm−1): 3435 (O-H), 2951, 2917, 2847 (C-H aliphatic); 1759 (C=O ester); 1624 (C=N); 1605, 1471 (C=C aromatic), 1095 (C-Cl).
1H NMR (400 MHz, CDCl3): δ/ppm 0.91 (t, 3H, J = 6.9 Hz, CH3), 1.28-1.44 {m, 28H, CH3(CH2)14-}, 1.78 (quint, 2H, J = 7.3 Hz, -CH2CH2COO-), 2.58 (t, 2H, J = 7.4 Hz, -CH2COO-), 6.71 (dd, 1H, J = 2.1, 8.4 Hz, Ar-H), 6.78 (d, 1H, J = 2.1 Hz, Ar-H), 7.21 (dd, 2H, J = 2.0, 8.6 Hz, Ar-H), 7.37 (dd, 2H, J = 2.3, 8.3 Hz, Ar-H), 7.39 (d, 1H, J = 8.4 Hz, Ar-H), 8.58 (s, 1H, CH=N), 13.31 (s, 1H, OH).
13C NMR (100 MHz, CDCl3): δ/ppm 171.8 (COO), 162.9 (CH=N), 162.4, 155.3, 147.3, 133.6, 133.0, 129.9, 122.7, 117.3, 113.3, 110.8 (aromatic carbons), 34.8 (-CH2COO-), 25.3 (-CH2CH2COO-), 32.3, 30.1, 30.0, 29.9, 29.8, 29.7, 29.6, 29.4, 23.0 (CH3(CH2)14-), 14.4 (CH3).
Elemental analysis: Calculated for C31H44ClNO3 C, 72.42%, H, 8.63%, N, 2.72%; Found: C, 72.30%, H, 8.71%, N, 2.75%.

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

Acknowledgements

The author (S.T. Ha) would like to thank Universiti Tunku Abdul Rahman for the financial support and research facilities.

References and Notes

  1. Hadjoudis, E.; Vittorakis, M.; Moustakali-Mavridis, I. Photochromism and thermochromism of schiff bases in the solid state and in rigid glasses. Tetrahedron 1987, 43, 1345–1360. [Google Scholar] [CrossRef]
  2. Hadjoudis, E.; Rontoyianni, A.; Ambroziak, K.; Dziembowska, T.; Mavridis, I.M. Photochromism and thermochromism of solid trans-N,N'-bis(salicylidene)-1,2-cyclohexanediamines and trans-N,N'-bis-(2-hydroxynaphylidene)-1,2-cyclohexanediamine. J. Photochem. Photobiol. A - Chem. 2004, 162, 521–530. [Google Scholar] [CrossRef]
  3. Oshima, A.; Momotake, A.; Arai, T. Photochromism, thermochromism, and solvatochromism of naphthalene-based analogues of salicylideneaniline in solution. J. Photochem. Photobiol. A - Chem. 2004, 162, 473–479. [Google Scholar] [CrossRef]
  4. Yeap, G.Y.; Ha, S.T.; Ishizawa, N.; Suda, K.; Boey, P.L.; Mahmood, W.A.K. Synthesis, crystal structure and spectroscopic study of para substituted 2-hydroxy-3-methoxybenzalideneanilines. J. Mol. Struct. 2003, 658, 87–99. [Google Scholar] [CrossRef]
  5. Yeap, G.Y.; Ha, S.T.; Lim, P.L.; Boey, P.L.; Ito, M.M.; Sanehisa, S.; Youhei, Y. Synthesis, physical and mesomorphic properties of Schiff’s base esters containing ortho-, meta- and para-substituents in benzylidene-4’-alkanoyloxyanilines. Liq. Cryst. 2006, 33, 205–211. [Google Scholar] [CrossRef]
  6. Ha, S.T.; Ong, L.K.; Wong, J.P.W.; Yeap, G.Y.; Lin, H.C.; Ong, S.T.; Koh, T.M. Mesogenic Schiff’s base ether with dimethylamino end group. Phase Transit. 2009, 82, 387–397. [Google Scholar] [CrossRef]
  7. Ha, S.T.; Ong, L.K.; Ong, S.T.; Yeap, G.Y.; Wong, J.P.W.; Koh, T.M.; Lin, H.C. Synthesis and mesomorphic properties of new Schiff base esters with different alkyl chains. Chin. Chem. Lett. 2009, 20, 767–770. [Google Scholar] [CrossRef]
  8. Ha, S.T.; Koh, T.M.; Ong, S.T.; Beh, J.K.; Ong, L.K. Synthesis of a new liquid crystal, 3-hydroxy-4-{[(6-methoxy-1,3-benzothiazol-2-yl)imino]methyl}phenyl palmitate. Molbank 2009, 2009, M608. [Google Scholar] [CrossRef]
  9. Ha, S.T.; Ong, L.K.; Yasodha, S.; Yeap, G.Y.; Boey, P.L.; Lin, H.C. New mesogenic Schiff base esters with polar chloro substituent: synthesis, thermotropic properties and X-ray diffraction studies. Am. J. Appl. Sci. 2010, 7, 214–220. [Google Scholar] [CrossRef]
  10. Ha, S.T.; Ong, S.T.; Chong, Y.T.; Yeap, G.Y. Synthesis of 4-{[(3-chlorophenyl)imino]methyl}-3-hydroxyphenyl myristate. Molbank 2009, 2009, M629. [Google Scholar] [CrossRef]

Share and Cite

MDPI and ACS Style

Ha, S.-T.; Ng, M.-Y.; Koh, T.-M.; Lee, T.-L. 3-Hydroxy-4-{[(4-chlorophenyl)imino]methyl}phenyl Octadecanoate. Molbank 2010, 2010, M674. https://doi.org/10.3390/M674

AMA Style

Ha S-T, Ng M-Y, Koh T-M, Lee T-L. 3-Hydroxy-4-{[(4-chlorophenyl)imino]methyl}phenyl Octadecanoate. Molbank. 2010; 2010(2):M674. https://doi.org/10.3390/M674

Chicago/Turabian Style

Ha, Sie-Tiong, Mei-Yoke Ng, Teck-Ming Koh, and Teck-Leong Lee. 2010. "3-Hydroxy-4-{[(4-chlorophenyl)imino]methyl}phenyl Octadecanoate" Molbank 2010, no. 2: M674. https://doi.org/10.3390/M674

APA Style

Ha, S. -T., Ng, M. -Y., Koh, T. -M., & Lee, T. -L. (2010). 3-Hydroxy-4-{[(4-chlorophenyl)imino]methyl}phenyl Octadecanoate. Molbank, 2010(2), M674. https://doi.org/10.3390/M674

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