3-Hydroxy-4-[(phenylimino)methyl]phenyl Myristate
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
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.
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%).
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 3Acknowledgements
The main author (S.T. Ha) would like to thank Universiti Tunku Abdul Rahman for the financial support and research facilities.
References and Notes
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© 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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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 StyleHa, 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
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