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Short Note

4-{[(4-Fluorophenyl)imino]methyl}-3-hydroxyphenyl 4-(Hexadecanoyloxy)benzoate

by
Sie-Tiong Ha
1,*,
Guan-Yeow Yeap
2 and
Peng-Lim Boey
2
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.
Molbank 2011, 2011(2), M723; https://doi.org/10.3390/M723
Submission received: 12 January 2011 / Accepted: 18 March 2011 / Published: 1 April 2011
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Abstract

:
A new Schiff base ester, 4-{[(4-fluorophenyl)imino]methyl}-3-hydroxyphenyl 4-(hexadecanoyloxy)benzoate was synthesized and its IR, 1H NMR, 13C NMR and EI-MS spectroscopic data are presented.

Graphical Abstract

Schiff bases have attracted much attention from many researchers owing to their thermochromic and photochromic properties [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 also been identified as one of the important requirements which favours the existence of liquid crystal phases [6,7,8]. Different alkyl chain length and terminal substituent can significantly influence the anisotropic properties of liquid crystals [6]. Thus, we report here another new derivative containing an hexadecanoyloxy chain, 4-{[(4-fluorophenyl)imino]methyl}-3-hydroxyphenyl 4-(hexadecanoyloxy)benzoate.
Molbank 2011 m723 sch001 550
Scheme 1. Synthesis of 4-{[(4-Fluorophenyl)imino]methyl}-3-hydroxyphenyl 4-(hexadecanoyloxy)benzoate.
Scheme 1. Synthesis of 4-{[(4-Fluorophenyl)imino]methyl}-3-hydroxyphenyl 4-(hexadecanoyloxy)benzoate.
Molbank 2011 m723 sch001

Experimental

Analytical data were obtained on Perkin Elmer 2400 LS series CHNS/O analyzers. Electron impact mass spectra (EI-MS) were recorded by Hewlett Packard 5989A Mass Spectrometer operating at 70 eV ionizing energy. FT-IR data were recorded on a Perkin Elmer 2000-FTIR spectrophotometer. NMR spectra were recorded in CDCl3 on a Bruker 400 MHz Ultrashield Spectrometer.
4-(4-n-Hexadecanoyloxybenzoyloxy)-2-hydroxybenzaldehye was prepared according to method described in our previous work [9]. In a round-bottom flask, a mixture of the aldehyde (2.48 g, 5.0 mmol), 4-fluoroaniline (0.56 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 (1.56 g, 53%).
Melting point: 189–191 °C
MS (EI): m/z (rel. int. %) = 590 (1) (M+).
IR (KBr): νmax (cm−1), 2953, 2916, 2848 (C-H aliphatic), 1755 (C=O of C15H31COO- fragment), 1743 (C=O of benzoate), 1625 (C=N), 1605 (C=C aromatic), 1282 (C-O).
1H NMR (400 MHz, CDCl3): δ/ppm, 0.91 (t, 3H, J = 6.8 Hz, CH3-), 1.24–1.47 (m, 24H, CH3-(CH2)12-), 1.79 (quint, 2H, J = 7.5 Hz, -CH2-CH2COO-), 2.62 (t, 2H, J = 7.5 Hz, -CH2-COO-), 6.86 (dd, 1H, J = 2.2, 8.4 Hz, Ar-H), 6.93 (d, 1H, J = 2.2 Hz, Ar-H), 7.12–7.17 (m, 2H, Ar-H), 7.26–7.31 (m, 4H, Ar-H), 7.46 (d, 1H, J = 8.5 Hz, Ar-H), 8.25 (d, 2H, J = 8.8 Hz, Ar-H), 8.62 (s, 1H, CH=N), 13.45 (s, 1H, OH).
13C NMR (100 MHz, CDCl3): δ/ppm, 171.86 (C=O of C15H31COO-), 164.11 (C=O of benzoate), 163.27 (C=N), 162.94, 161.94, 155.64, 155.14, 144.93, 133.54, 132.17, 127.08, 122.92, 122.25, 117.62, 116.49, 113.33 and 110.95 for aromatic carbons, 34.81 (-CH2COO-), 25.28 (-CH2CH2COO-), 32.27, 30.03, 30.02, 30.00, 29.98, 29.94, 29.79, 29.68, 29.58, 29.46, 23.01 (CH3(CH2)12), 14.37 (CH3(CH2)12).
Elemental analysis: Calculated for C36H44NO5F, 73.32%, H, 7.52%, N, 2.38%; Found: C, 73.37%, H, 7.50%, N, 2.40%.

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

Acknowledgements

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

References

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Share and Cite

MDPI and ACS Style

Ha, S.-T.; Yeap, G.-Y.; Boey, P.-L. 4-{[(4-Fluorophenyl)imino]methyl}-3-hydroxyphenyl 4-(Hexadecanoyloxy)benzoate. Molbank 2011, 2011, M723. https://doi.org/10.3390/M723

AMA Style

Ha S-T, Yeap G-Y, Boey P-L. 4-{[(4-Fluorophenyl)imino]methyl}-3-hydroxyphenyl 4-(Hexadecanoyloxy)benzoate. Molbank. 2011; 2011(2):M723. https://doi.org/10.3390/M723

Chicago/Turabian Style

Ha, Sie-Tiong, Guan-Yeow Yeap, and Peng-Lim Boey. 2011. "4-{[(4-Fluorophenyl)imino]methyl}-3-hydroxyphenyl 4-(Hexadecanoyloxy)benzoate" Molbank 2011, no. 2: M723. https://doi.org/10.3390/M723

APA Style

Ha, S. -T., Yeap, G. -Y., & Boey, P. -L. (2011). 4-{[(4-Fluorophenyl)imino]methyl}-3-hydroxyphenyl 4-(Hexadecanoyloxy)benzoate. Molbank, 2011(2), M723. https://doi.org/10.3390/M723

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