Comparing of 5-Nonylsalicylaldoxime and Salicylaldehyde Characterization Using Magnesium Salt Formylation Process

  • Pouramini, Zeinab ;
  • Moradi, Ali
  • Received : 2012.02.19
  • Accepted : 2012.05.22
  • Published : 2012.06.20


5-Nonylsalicylaldoxime and salicylaldehyde are two derivatives of phenolic compounds which are very applicable materials in industries. Formerly the formylation of phenolic derivatives were carried out by Rimer-Tiemann method. In this work both of these two materials were synthesized by magnesium meditated formylation technique and their structural characterizations were compared by instrumental analysis technique. In order to achieve a selectively orthoformylated product, the hydroxyl group of nonylphenol (or phenol) was first modified by magnesium methoxide. The nonylphenol magnesium salt was then formylated by paraformaldehyde. The oximation reaction was finally applied to the prepared nonylsalicylaldehyde magnesium salt by liquid extracting via water and acid washing and other extractions. The solvent was finally removed by evaporation under reduced pressure. Some instrumental analysis such as $^1H$-NMR, GC/MS and FT-IR spectra were taken on the product in order to interpret the reaction characterization quantitatively and qualitatively. The formaldehyde and oxime functional groups of two compounds were investigated through $^1H$-NMR and FT-IR spectra and were compared. The yield of methoxilation was very good and the yields of formylation and oximation reactions were about 90%and 85% respectively. The orthoselectivity of formylation reaction were evaluated by comparing of the relevant spectra. The GC/MS spectra also confirmed the obtained results.




  1. Kordosky, G. A. Solvent Extraction Reagents and Applications; MCT Redbook, Cognis Corporation Publisher: U.S.A., 2007.
  2. Smith, A. G.; Tasker, P. A.; White, D. J. Coord. Chem. Rev. 2003, 241, 61.
  3. Habbache, N.; Alane, N.; Djerad S.; Tifouti, L. Chem. Eng. J. 2009, 152, 503.
  4. Forgan, R. S. Ph.D. Thesis, University of Edinburgh, 2008.
  5. Ritcey, G. M.; Singhua, T. Sci. Tech. 2006, 11, 137.
  6. Kirk, R. E.; Othmer, D. F. Encyclopedia of Chemical Technology, 4th ed.; Wiley: New York, 1991; pp 1030-1042.
  7. Vogel, A. I. A Text Book of Organic Chemistry; Addison-Wesley Pub. Co.: 1991.
  8. Thoer, A.; Denis, G.; Delmas, M.; Gaset, A. U.S. Pat. 4755613, 1988.
  9. Aldred, R.; Johnston, R.; Levin, D.; Neilan, J. J. Chem. Soc., Perkin Trans. 1994, 1, 1823.
  10. Levin, D. U.S. Pat. 5502254, 1996.
  11. Dimmite, J. H.; Kearns, M. A.; Chambless, W. H. U.S. Pat. 6288276, 2001.
  12. Matsuda, T.; Murata, T. U.S. Pat. 4231967, 1980.
  13. Beswick, G. E. U.S. Pat. 4085146, 1978.
  14. Paliwal, S. B.; Mathur, V. B.; Mirani, B. N. WO 2007/034501, 2007.
  15. Lindoy, L. F.; Meehan, G. V.; Svenstrup, N. Synthesis 1998, 1029.
  16. Casiraghi, G.; Casnati, G.; Cornia, M.; Pochini, A.; Puglia, G.; Sartori, G.; Ungaro, R. J. Chem. Soc. Perkin Trans. 1978, 1, 318.
  17. Willemse, J. A., MSc. Thesis, University of Rand Afrikaans, 2003.
  18. Hofslokken, N. U.; Skatteboll, L. Acta Chemica Scandinavica 1999, 258.
  19. Kasler, F. Quantitative Analysis by NMR Spectroscopy; Academic Press Inc.: London and New York, 1973; p 130.
  20. Silverstein, R. M.; Bassler G. C.; T. C., Morill Spectrometric Identification of Organic Compounds; John Wiley & Sons: New York, 1991.
  21. Mohan, J. Organic Spectroscopy: Principles and Applications; Narosa Publishing House: India, 2000.

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