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3-Hydroxy-4-{[(4-chlorophenyl)imino]methyl}phenyl Octadecanoate
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Volume 2010
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Short Note

3-Hydroxy-4-{[(4-fluorophenyl)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), M673; https://doi.org/10.3390/M673
Submission received: 25 March 2010 / Accepted: 8 April 2010 / Published: 9 April 2010
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Abstract

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

Graphical Abstract

Schiff base (CH=N) compounds have received a considerable amount of attention from many sresearchers owing to their importance in exhibiting thermochromism and photochromism [1,2,3]. Aromatic Schiff bases possessing a long alkyl chain have received overwhelming attention due to their possibility to show liquid crystallinity properties such as smectic and nematic phases [4,5,6,7].

Synthesis

4-Formyl-3-hydroxyphenyl octadecanoate was previously prepared via Steglich esterification [8]. In a round-bottom flask, a mixture of the aldehyde I (1.74 g, 5.0 mmol), 4-fluoroaniline (0.56 g, 5.0 mmol) and absolute ethanol (40 mL) was refluxed for 3 h with stirring. 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 (1.84 g, 74%).
Molbank 2010 m673 i001
Melting point: 95.4 °C
MS (EI): m/z = 497 (M+)
IR (KBr, cm−1): 3454 (O-H), 2954, 2918, 2849 (C-H aliphatic); 1758 (C=O ester); 1624 (C=N); 1609, 1510 (C=C aromatic), 1245 (C-F).
1H NMR (400 MHz, CDCl3): δ/ppm 0.89 (t, 3H, J = 7.0 Hz, CH3), 1.28-1.45 {m, 28H, CH3(CH2)14-}, 1.74 (quint, 2H, J = 7.3 Hz, -CH2CH2COO-), 2.56 (t, 2H, J = 7.5 Hz, -CH2COO-), 6.71 (dd, 1H, J = 2.2, 8.4 Hz, Ar-H), 6.78 (d, 1H, J = 2.2 Hz, Ar-H), 7.10 (m, 2H, Ar-H), 7.25 (m, 2H, Ar-H), 7.38 (d, 1H, J = 8.4 Hz, Ar-H), 8.58 (s, 1H, CH=N), 13.39 (s, 1H, OH).
13C NMR (100 MHz, CDCl3): δ/ppm 172.1 (COO), 162.8 (CH=N), 161.9, 160.9, 155.0, 144.8, 133.5, 123.0, 117.4, 116.7, 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, 29.5, 23.1 (CH3(CH2)14-), 14.5 (CH3).
Elemental analysis: Calculated for C31H44FNO3 C, 74.81%, H, 8.91%, N, 2.81%; Found: C, 74.92%, H, 8.98%, N, 2.70%.

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.; 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]
  5. 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]
  6. 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]
  7. 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]
  8. 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-fluorophenyl)imino]methyl}phenyl Octadecanoate. Molbank 2010, 2010, M673. https://doi.org/10.3390/M673

AMA Style

Ha S-T, Ng M-Y, Koh T-M, Lee T-L. 3-Hydroxy-4-{[(4-fluorophenyl)imino]methyl}phenyl Octadecanoate. Molbank. 2010; 2010(2):M673. https://doi.org/10.3390/M673

Chicago/Turabian Style

Ha, Sie-Tiong, Mei-Yoke Ng, Teck-Ming Koh, and Teck-Leong Lee. 2010. "3-Hydroxy-4-{[(4-fluorophenyl)imino]methyl}phenyl Octadecanoate" Molbank 2010, no. 2: M673. https://doi.org/10.3390/M673

APA Style

Ha, S. -T., Ng, M. -Y., Koh, T. -M., & Lee, T. -L. (2010). 3-Hydroxy-4-{[(4-fluorophenyl)imino]methyl}phenyl Octadecanoate. Molbank, 2010(2), M673. https://doi.org/10.3390/M673

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