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25 June 2012

3-Hydroxy-4-[(phenylimino)methyl]phenyl 4-(Hexadecanoyloxy)benzoate

,
and
1
Department of Chemical Science, Faculty of Science, Universiti Tunku Abdul Rahman, Jln Universiti, Bandar Barat, 31900 Kampar, Perak, Malaysia
2
Liquid Crystal Research Laboratory, School of Chemical Sciences, Universiti Sains Malaysia, 11800 Minden, Penang, Malaysia
*
Author to whom correspondence should be addressed.
Molbank2012, 2012(3), M762;https://doi.org/10.3390/M762
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Abstract

A new Schiff base ester, 3-hydroxy-4-[(phenylimino)methyl]phenyl 4-(hexadecanoyloxy)benzoate was synthesized and its IR, 1H-NMR, 13C-NMR and MS spectroscopic data are presented.
Mesomorphic materials have many practical applications, in particular as display devices, organic light emitting diodes, anisotropic networks, photoconductors and semiconductor materials [1,2,3]. Strong demand of new mesomorphic compounds for applications has encouraged the synthesis and study of numerous mesogens in particular, thermotropic liquid crystals [4,5]. Wide-ranging research on Schiff base core systems has been carried out since the discovery of MBBA, which exhibited room temperature nematic phase [6]. Several studies have been conducted on ester type of Schiff bases due to their interesting properties and substantial temperature range [7,8,9,10,11,12,13]. Thus, we report here another new derivative containing an hexadecanoyloxy chain, 3-hydroxy-4-[(phenylimino)methyl]phenyl 4-(hexadecanoyloxy)benzoate.

Experimental

4-(4-n-Hexadecanoyloxybenzoyloxy)-2-hydroxybenzaldehye was prepared according to a method that was described in our previous work [13]. In a round-bottom flask, a mixture of the aldehyde (2.48 g, 5.0 mmol), aniline (0.47 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 (1.14 g, 40%).
Melting point: 153–154 °C
MS (EI): m/z (rel. int. %) = 572 (1) (M+).
IR (KBr): νmax/ cm−1 2953, 2916, 2848 (C-H aliphatic), 1752 (C=O of C15H31COO- fragment), 1743 (C=O of benzoate), 1628 (C=N), 1605 (C=C aromatic), 1283 (C-O).
1H-NMR (400 MHz, CDCl3): δ/ppm 0.90 (t, 3H, J = 6.5 Hz, CH3-), 1.22–1.42 (m, 24H, CH3-(CH2)12-), 1.80 (quint, 2H, J = 7.2 Hz, -CH2-CH2COO-), 2.63 (t, 2H, J = 7.4 Hz, -CH2-COO-), 6.86 (dd, 1H, J = 2.2, 8.4 Hz, Ar-H), 6.92 (d, 1H, J = 2.2 Hz, Ar-H), 7.26–7.34 (m, 5H, Ar-H), 7.40–7.48 (m, 3H, Ar-H), 8.26 (dd, 2H, J = 2.3, 8.7 Hz, Ar-H), 8.66 (s, 1H, CH=N), 13.67 (s, 1H, O-H).
13C-NMR (100 MHz, CDCl3): δ/ppm 172.09 (C=O of C15H31COO-), 164.25 (C=O of benzoate), 162.17 (C=N), 163.0, 155.5, 155.0, 148.6, 133.6, 132.3, 129.9, 127.0, 126.8, 122.3, 121.6, 117.7, 113.3 and 111.0 for aromatic carbons, 34.8 (-CH2COO-), 25.3 (-CH2CH2COO-), 32.3, 30.1, 30.0, 29.9, 29.8, 29.7, 29.5, 23.1 (CH3(CH2)12), 14.5 (CH3(CH2)12).
Elemental analysis: Calculated for C36H45NO5, 75.63%, H, 7.93%, N, 2.45%; Found: C, 75.66%, H, 7.91%, N, 2.44%.

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

Acknowledgments

Authors would like to thank Universiti Tunku Abdul Rahman and Universitit Sains Malaysia for the financial supports and research facilities.

References and Notes

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