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

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.

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Molbank 2009, M632

molbank
ISSN 1422-8599
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Short Note
3-Hydroxy-4-[(phenylimino)methyl]phenyl Myristate
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; E-Mail: hast@utar.edu.my or
hast_utar@yahho.com.
Received: 26 August 2009 / Accepted: 13 October 2009 / Published: 14 October 2009


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.

Keywords: 3-hydroxy-4-[(phenylimino)methyl]phenyl myristate; Schiff base; alkyl chain


Schiff bases have received a considerable amount of attention from many researchers owing to their
importance in exhibiting thermochromism and photochromism [1–4]. 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 [5–9].

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%).
OPEN ACCESS

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C2H5OH
C13H27COO
OH
O
C13H27COO
+
NH2
OH
N


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%.

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.
2. Hadjoudis, E.; Rontoyianni, A.; Ambroziak, K.; Dziembowska, T.; Mavridis, I.M.
Photochromism and thermochromism
cyclohexanediamines and
trans-N,N'-bis-(2-hydroxynaphylidene)-1,2-cyclohexanediamine.
J. Photochem. Photobiol. A: Chem. 2004, 162, 521–530.
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.
of solid
trans-N,N'-bis(salicylidene)-1,2-

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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.
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.
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.
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.
8. Ha, S.T.; Ong, L.K.; Win,
ylmethylene)amino]phenyltetradecanoate. Molbank 2009, 2009, M585.
9. Ha, S.T.; Ong, L.K.; Win,
ylmethylene)amino]phenylhexadecanoate. Molbank 2009, 2009, M584.
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.

© 2009 by the authors; licensee Molecular Diversity Preservation International, Basel, Switzerland.
This article is an open-access article distributed under the terms and conditions of the Creative
Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
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Y.F.; Koh, T.M. 4-[(Pyridin-3-
Y.F.; Koh, T.M. 4-[(Pyridin-3-