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Volume 2009
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10.3390/M632
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Short Note

3-Hydroxy-4-[(phenylimino)methyl]phenyl Myristate

by
Sie-Tiong Ha
1,*,
Siew-Teng Ong
1,
Yee-Ting Chong
2 and
Guan-Yeow Yeap
3
1
Department of Chemical Science, Faculty of Science, Universiti Tunku Abdul Rahman, Jln Universiti, Bandar Barat, 31900 Kampar, Perak, Malaysia
2
Department of Science & Engineering, Centre for Foundation Studies, Universiti Tunku Abdul Rahman, Building PE, No. 1 Jalan 13/4, 46200 Petaling Jaya, Selangor, Malaysia
3
Liquid Crystal Research Laboratory, School of Chemical Sciences, Universiti Sains Malaysia, Minden 11800 Minden, Penang, Malaysia
*
Author to whom correspondence should be addressed.
Molbank 2009, 2009(4), M632; https://doi.org/10.3390/M632
Submission received: 26 August 2009 / Accepted: 13 October 2009 / Published: 14 October 2009
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Abstract

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

Graphical Abstract

Schiff bases have received a considerable amount of attention from many researchers owing to their importance in exhibiting thermochromism and photochromism [1,2,3,4]. Aromatic Schiff bases possessing long alkyl chain have received much attention due to their possibility to exhibit liquid crystalline properties such as smectic and nematic phases [5,6,7,8,9].

Synthesis

4-Formyl-3-hydroxyphenyl tetradecanoate was previously prepared via Steglich esterification [10]. In a round-bottom flask, a mixture of the 4-formyl-3-hydroxyphenyl tetradecanoate (1.74 g, 5.0 mmol), aniline (0.47 g, 5.0 mmol) and absolute ethanol (50 mL) was refluxed with stirring for three hours. The reaction mixture was filtered and the solvent removed from the filtrate by evaporation. Recrystallization from absolute ethanol gave the title compound as yellow solid (1.14 g, 54%).
Molbank 2009 m632 g001
Melting point: 103.4 oC.
MS(EI): M+ (m/z) = 423 (4) [M]+, 213 (100).
IR (KBr, cm-1): 3435 (O-H), 2952, 2917, 2848 (C-H aliphatic); 1754 (C=O ester); 1629 (C=N); 1594, 1499 (C=C aromatic).
1H NMR (400 MHz, CDCl3): δ/ppm 0.90 (t, 3H, J = 6.9 Hz, CH3), 1.30-1.46 {m, 20H, CH3(CH2)10-}, 1.75 (q, 2H, J = 7.5 Hz, -CH2CH2COO-), 2.57 (t, 2H, J = 7.5 Hz, -CH2COO-), 6.71 (dd, 1H, J = 2.2, 8.4 Hz, Ar-H), 6.79 (d, 1H, J = 2.2 Hz, Ar-H), 7.28 (m, 3H, Ar-H), 7.39 (d, 1H, J = 8.4 Hz, Ar-H), 7.42 (m, 2H, Ar-H), 8.62 (s, 1H, CH=N), 13.60 (s, 1H, OH).
13C NMR (100 MHz, CDCl3): δ/ppm 172.1 (COO), 162.2 (CH=N), 163.0, 154.9, 148.6, 133.5, 129.8, 127.4, 121.6, 117.5, 113.3, 110.9 (aromatic carbons), 34.86 (-CH2COO-), 25.30 (-CH2CH2COO-), 32.34, 30.10, 30.07, 30.02, 29.88, 29.78, 29.67, 29.50, 23.11 (CH3(CH2)14-), 14.54 (CH3).
Elemental analysis: Calculated for C27H37NO3 C, 76.56%, H, 8.80%, N, 3.31%; Found: C, 76.45%, H, 8.87%, N, 3.44%.

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

Acknowledgements

The main 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]
  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]
  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. 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 Transitions 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.; 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]
  8. Ha, S.T.; Ong, L.K.; Win, Y.F.; Koh, T.M. 4-[(Pyridin-3-ylmethylene)amino]phenyltetradecanoate. Molbank 2009, 2009, M585. [Google Scholar] [CrossRef]
  9. Ha, S.T.; Ong, L.K.; Win, Y.F.; Koh, T.M. 4-[(Pyridin-3-ylmethylene)amino]phenylhexadecanoate. Molbank 2009, 2009, M584. [Google Scholar] [CrossRef]
  10. Ha, S.T.; Ong, S.T.; Chong, Y.T.; Yeap, G.Y. 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.; Ong, S.-T.; Chong, Y.-T.; Yeap, G.-Y. 3-Hydroxy-4-[(phenylimino)methyl]phenyl Myristate. Molbank 2009, 2009, M632. https://doi.org/10.3390/M632

AMA Style

Ha S-T, Ong S-T, Chong Y-T, Yeap G-Y. 3-Hydroxy-4-[(phenylimino)methyl]phenyl Myristate. Molbank. 2009; 2009(4):M632. https://doi.org/10.3390/M632

Chicago/Turabian Style

Ha, Sie-Tiong, Siew-Teng Ong, Yee-Ting Chong, and Guan-Yeow Yeap. 2009. "3-Hydroxy-4-[(phenylimino)methyl]phenyl Myristate" Molbank 2009, no. 4: M632. https://doi.org/10.3390/M632

APA Style

Ha, S. -T., Ong, S. -T., Chong, Y. -T., & Yeap, G. -Y. (2009). 3-Hydroxy-4-[(phenylimino)methyl]phenyl Myristate. Molbank, 2009(4), M632. https://doi.org/10.3390/M632

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