Next Article in Journal
2,2'-Thio-bis[(4-methylphenyl)-2-aminobenzoate]
Previous Article in Journal
3-(1H-Indol-3-yl)-4-(morpholin-4-yl)cyclobut-3-ene-1,2-dione
 
 
Search for Articles:
Title / Keyword
Author / Affiliation / Email
Journal
Article Type
 
 
Advanced Search
 
Section
Special Issue
Volume
Issue
Number
Page
 
Journals
Molbank
Volume 2012
Issue 2
10.3390/M759
molbank-logo
Submit to this Journal Review for this Journal Propose a Special Issue
► Article Menu

Article Menu

share Share announcement Help format_quote Cite question_answer Discuss in SciProfiles thumb_up
...
Endorse textsms
...
Comment
first_page
settings
Order Article Reprints
Font Type:
Arial Georgia Verdana
Font Size:
Aa Aa Aa
Line Spacing:
Column Width:
Background:
Short Note

4-{[(4-Chlorophenyl)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 2012, 2012(2), M759; https://doi.org/10.3390/M759
Submission received: 20 April 2012 / Accepted: 29 May 2012 / Published: 7 June 2012
Browse Figures
Versions Notes

Abstract

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

Graphical Abstract

Benzylideneanilines (Schiff bases) exhibit very interesting thermochromic and photochromic properties. Therefore, they became a topic of numerous recent publications [1,2,3,4,5,6]. Flexible long alkyl chain at the para position of N-benzylideneanilines has also been viewed as one of the important criteria for exhibition of liquid crystal phases [7,8,9,10]. Different alkyl chain length and terminal substituent can significantly influence the anisotropic properties of liquid crystals [7,8]. Thus, we report here another new derivative containing an hexadecanoyloxy chain, 4-{[(4-chlorophenyl)imino]methyl}-3-hydroxyphenyl 4-(hexadecanoyloxy)benzoate.
Molbank 2012 m759 sch001 550
Scheme 1. Synthesis of 4-{[(4-chlorophenyl)imino]methyl}-3-hydroxyphenyl 4-(hexadecanoyloxy)benzoate.
Scheme 1. Synthesis of 4-{[(4-chlorophenyl)imino]methyl}-3-hydroxyphenyl 4-(hexadecanoyloxy)benzoate.
Molbank 2012 m759 sch001

Experimental

4-(4-n-Hexadecanoyloxybenzoyloxy)-2-hydroxybenzaldehye was prepared according to method that described in our previous work [11]. In a round-bottom flask, a mixture of the aldehyde (2.48 g, 5.0 mmol), 4-chloroaniline (0.64 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 (1.88 g, 62%).
Melting point: 214–215 °C.
MS (EI): m/z (rel. int. %) = 606 (1) (M+).
IR (KBr): νmax/ cm−1 3400 (broad, O-H), 2951, 2916, 2848 (C-H aliphatic), 1755 (C=O of C15H31COO- fragment), 1743 (C=O of benzoate), 1625 (C=N), 1604 (C=C aromatic), 1282 (C-O).
1H-NMR (400 MHz, CDCl3): δ/ppm 0.92 (t, 3H, J = 6.7 Hz, CH3-), 1.25–1.53 (m, 24H, CH3-(CH2)12-), 1.80 (quint, 2H, J = 7.4 Hz, -CH2-CH2COO-), 2.62 (t, 2H, J = 7.5 Hz, -CH2-COO-), 6.87 (dd, 1H, J = 2.2, 8.4 Hz, Ar-H), 6.94 (d, 1H, J = 2.1 Hz, Ar-H), 7.23–7.29 (m, 4H, Ar-H), 7.40–7.43 (m, 2H, Ar-H), 7.45 (d, 1H, J = 8.4 Hz, Ar-H), 8.25 (d, 2H, J = 8.6 Hz, Ar-H), 8.63 (s, 1H, CH=N), 13.26 (s, 1H, OH).
13C-NMR (100 MHz, CDCl3): δ/ppm 171.9 (C=O of C15H31COO-), 164.3 (C=O of benzoate), 162.5 (C=N), 163.0, 155.7, 155.3, 147.3, 133.7, 133.1, 132.2, 130.0, 127.1, 122.8, 122.3, 117.6, 113.4 and 111.0 for aromatic carbons, 34.8 (-CH2COO-), 25.2 (-CH2CH2COO-), 32.3, 30.1, 30.0, 29.9, 29.8, 29.7, 29.6, 29.5, 23.0 (CH3(CH2)12), 14.4 (CH3(CH2)12).
Elemental analysis: Calculated for C36H44NO5Cl, 71.33%, H, 7.32%, N, 2.31%; Found: C, 71.36%, H, 7.30%, N, 2.32%.

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

Acknowledgements

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

References and Notes

  1. Kosar, B.; Albayrak, C.; Ersanli, C.C.; Odabasoglu, M.; Buyukgungor, O. Molecular structure, spectroscopic investigations, second-order nonlinear optical properties and intramolecular proton transfer of (E)-5-(diethylamino)-2-[(4-propylphenylimino)methyl]phenol: A combined experimental and theoretical study. Spectrochim. Acta A 2012, 93, 1–9. [Google Scholar] [CrossRef] [PubMed]
  2. Hadjoudis, E.; Yannakopoulou, K.; Chatziefthimiou, S.D.; Paulidou, A.; Mavridis, I.M. Supramolecular control of photochromism in a β-cyclodextrin/Schiff base system. J. Photochem. Photobiol. A Chem. 2011, 217, 293–298. [Google Scholar] [CrossRef]
  3. Naganagowda, G.; Petsom, A. 4-Amino-N-(2-hydroxy-4-pentadecylbenzylidene)-benzenesulfonamide. Molbank 2011, 2011, M739. [Google Scholar] [CrossRef]
  4. 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]
  5. 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] [CrossRef]
  6. 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]
  7. Yeap, G.Y.; Ha, S.T.; Lim, P.L.; Boey, P.L.; Ito, M.M.; Sanehisa, S.; Youhei, Y. Synthesis, physical and mesomorphic properties of Schiff’s base esters containing ortho-, meta- and para-substituents in benzylidene-4'-alkanoyloxyanilines. Liq. Cryst. 2006, 33, 205–211. [Google Scholar] [CrossRef]
  8. Godzwon, J.; Sienkowska, M.J.; Galewski, Z. Liquid-crystalline polymorphism of 4-heptyloxybenzylidene-4'- alkyloxyanilines and their phase equilibrium with 4-octyloxyphenyl 4-nitrobenzoate. Thermochim. Acta 2012, 531, 75–82. [Google Scholar] [CrossRef]
  9. 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 Transit. 2009, 82, 387–397. [Google Scholar] [CrossRef]
  10. 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]
  11. Yeap, G.Y.; Ha, S.T.; Boey, P.L.; Mahmood, W.A.K.; Ito, M.M.; Youhei, Y. Synthesis and characterization of some new mesogenic Schiff base esters N-[4-(4-n-hexadecanoyloxybenzoyloxy)benzylidene]-4-substituted anilines. Mol. Cryst. Liq. Cryst. 2006, 452, 73–90. [Google Scholar] [CrossRef]

Share and Cite

MDPI and ACS Style

Ha, S.-T.; Yeap, G.-Y.; Boey, P.-L. 4-{[(4-Chlorophenyl)imino]methyl}-3-hydroxyphenyl 4-(Hexadecanoyloxy)benzoate. Molbank 2012, 2012, M759. https://doi.org/10.3390/M759

AMA Style

Ha S-T, Yeap G-Y, Boey P-L. 4-{[(4-Chlorophenyl)imino]methyl}-3-hydroxyphenyl 4-(Hexadecanoyloxy)benzoate. Molbank. 2012; 2012(2):M759. https://doi.org/10.3390/M759

Chicago/Turabian Style

Ha, Sie-Tiong, Guan-Yeow Yeap, and Peng-Lim Boey. 2012. "4-{[(4-Chlorophenyl)imino]methyl}-3-hydroxyphenyl 4-(Hexadecanoyloxy)benzoate" Molbank 2012, no. 2: M759. https://doi.org/10.3390/M759

APA Style

Ha, S. -T., Yeap, G. -Y., & Boey, P. -L. (2012). 4-{[(4-Chlorophenyl)imino]methyl}-3-hydroxyphenyl 4-(Hexadecanoyloxy)benzoate. Molbank, 2012(2), M759. https://doi.org/10.3390/M759

Note that from the first issue of 2016, this journal uses article numbers instead of page numbers. See further details here.

Article Metrics

Back to TopTop