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Volume 2010
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Short Note

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

by
Sie-Tiong Ha
1,*,
Jun-Kit Beh
2,
Kok-Leei Foo
1,2,
Teck-Ming Koh
2,† and
Siew-Teng Ong
1
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 Kelang, 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), M686; https://doi.org/10.3390/M686
Submission received: 2 April 2010 / Accepted: 4 June 2010 / Published: 8 June 2010
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Abstract

:
A new Schiff base ester, 3-hydroxy-4-{[(4-methoxyphenyl)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 attention from many researchers owing to their importance in exhibiting thermochromism and photochromism [1,2,3,4,5]. 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 [6,7,8]. Different alkyl chain length can significantly influence the anisotropic properties of liquid crystals [6]. Thus, we report here another new derivative containing an octadecanoyloxy chain, 3-hydroxy-4-{[(4-methoxyphenyl)imino]methyl}phenyl octadecanoate.
Molbank 2010 m686 sch001 550
Scheme 1. Synthesis of 3-hydroxy-4-{[(4-methoxyphenyl)imino]methyl}phenyl octadecanoate.
Scheme 1. Synthesis of 3-hydroxy-4-{[(4-methoxyphenyl)imino]methyl}phenyl octadecanoate.
Molbank 2010 m686 sch001

Experimental

4-Formyl-3-hydroxyphenyl octadecanoate was previously prepared via Steglich esterification [9]. In a round-bottom flask, a mixture of the aldehyde (1.74 g, 5.0 mmol), 4-methoxyaniline (0.62 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 (1.10 g, 43%).
Melting point: 100.1 °C
MS (EI): m/z (rel. int. %) = 509 (1) (M+), 243 (100).
IR (KBr, cm−1): 3449 (O-H), 2955, 2918, 2849 (C-H aliphatic); 1759 (C=O ester); 1624 (C=N); 1605, 1510 (C=C aromatic).
1H NMR (400 MHz, CDCl3): δ/ppm 0.91 (t, 3H, J = 7.0 Hz, CH3), 1.27–1.44 {m, 28H, CH3(CH2)14-}, 1.78 (quint, 2H, J = 7.4 Hz, -CH2CH2COO-), 2.58 (t, 2H, J = 7.5 Hz, -CH2COO-), 3.85 (s, 3H, OCH3), 6.70 (dd, 1H, J = 2.2, 8.4 Hz, Ar-H), 6.76 (d, 1H, J = 2.2 Hz, Ar-H), 6.96 (dd, 2H, J = 2.1, 8.9 Hz, Ar-H), 7.28 (dd, 2H, J = 2.1, 8.9 Hz, Ar-H), 7.37 (d, 1H, J = 8.3 Hz, Ar-H), 8.60 (s, 1H, CH=N), 13.76 (s, 1H, OH).
13C NMR (100 MHz, CDCl3): δ/ppm 172.2 (COO), 159.9 (CH=N), 162.8, 159.3, 154.5, 141.5, 133.1, 122.7, 117.7, 115.0, 113.1, 110.7 (aromatic carbons), 55.93 (Ar-OCH3), 34.85 (-CH2COO-), 25.31 (-CH2CH2COO-), 32.33, 30.10, 30.07, 30.01, 29.87, 29.78, 29.67, 29.50, 23.10 (CH3(CH2)14-), 14.53 (CH3(CH2)14).
Elemental analysis: Calculated for C32H47NO4 C, 75.40%, H, 9.29%, N, 2.75%; Found: C, 75.29%, H, 9.37%, N, 2.81%.

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

Acknowledgements

The author (S.T. Ha) would like to thank Universiti Tunku Abdul Rahman (UTAR) for the UTAR Research Fund 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. Nair, S.M.; Bhattacharya, I. Synthesis and physiological activities of some imines and their β-lactams. Asian. J. Chem. 2009, 21, 504–510. [Google Scholar]
  6. 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]
  7. 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]
  8. 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]
  9. 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.; Beh, J.-K.; Foo, K.-L.; Koh, T.-M.; Ong, S.-T. 3-Hydroxy-4-{[(4-methoxyphenyl)imino]methyl}phenyl Octadecanoate. Molbank 2010, 2010, M686. https://doi.org/10.3390/M686

AMA Style

Ha S-T, Beh J-K, Foo K-L, Koh T-M, Ong S-T. 3-Hydroxy-4-{[(4-methoxyphenyl)imino]methyl}phenyl Octadecanoate. Molbank. 2010; 2010(2):M686. https://doi.org/10.3390/M686

Chicago/Turabian Style

Ha, Sie-Tiong, Jun-Kit Beh, Kok-Leei Foo, Teck-Ming Koh, and Siew-Teng Ong. 2010. "3-Hydroxy-4-{[(4-methoxyphenyl)imino]methyl}phenyl Octadecanoate" Molbank 2010, no. 2: M686. https://doi.org/10.3390/M686

APA Style

Ha, S. -T., Beh, J. -K., Foo, K. -L., Koh, T. -M., & Ong, S. -T. (2010). 3-Hydroxy-4-{[(4-methoxyphenyl)imino]methyl}phenyl Octadecanoate. Molbank, 2010(2), M686. https://doi.org/10.3390/M686

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