GREEN CHEMISTRY APPLICATION FOR THE SYNTHESIS OF (1)-N-4’-METHOXYBENZYL-1,10-PHENANTHROLINIUM BROMIDE

https://doi.org/10.22146/ijc.21611

Maulidan Firdaus(1*), Jumina Jumina(2), Chairil Anwar(3)

(1) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Sebelas Maret University, Jl. Ir Sutami 36A Surakarta
(2) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Sekip Utara, Yogyakarta 55281
(3) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Sekip Utara, Yogyakarta 55281
(*) Corresponding Author

Abstract


A simple, energy-efficient, and relatively quick synthetic procedure for the synthesis of (1)-N-4'-methoxybenzyl-1,10-phenanthrolinium bromide, based on green chemistry principles has been carried out. The synthesis was started by solvent-free reduction of p-anisaldehyde with NaBH4 to give 4-methoxybenzyl alcohol in 98% yield to be followed by solvent-free treatment of the resulted alcohol with PBr3 to yield 4-methoxybenzyl bromide (86%). Furthermore, the obtained bromide was reacted with 1,10-phenanthroline in acetone at reflux for 12 h to give the phenanthrolinium salt target in 68% yield.


Keywords


green chemistry; p-anisaldehyde; (1)-N-4'-methoxybenzyl-1,10-phenanthrolinium bromide

Full Text:

Full Text Pdf


References

[1] Anastas, P.T., and Warner, J.C., 1998, Green Chemistry: Theory and Practice, Oxford University Press, Oxford.

[2] Metzger, J.O. and Eissen, M., 2004, C. R. Chimie, 7, 1 – 13.

[3] Metzger, J.O., 1998, Angew. Chem. Int. Ed., 37 (21), 2975 – 2978.

[4] Yapi, A.D., Mustofa, M., Valentin, A., Chavignon, O., Teulade, J.C., Mallie, M., Chapat, J., and Blace, Y., 2000, Chem. Pharm. Bull., 48 (12), 1886 – 1889.

[5] Yapi, A.D., Valentin, A., Chezal, J.M., Chavignon, O., Chaillot, B., Gerhardt, R., Teulade, J.C., and Blace, Y., 2006, Arch. Pharm. Chem. Life Sci., 339, 201 – 206.

[6] Wijayanti, M.A., Sholikhah, E.N., Tahir, I., Hadanu, R., Jumina, Supargiyono, and Mustofa, 2006, J. Health Sci., 52 (6), 794 – 799.

[7] Hadanu, R., Matsjeh, S., Jumina, Mustofa, Wijayanti, M.A., and Sholikhah, E.W., 2007, Synthesis and Test Antiplasmodial Activitiest of (1)–N–4’–Methoxybenzyl–1,10–phenanthrolinium bromide Compound, 1st International Conference on Chemical Sciences proceeding, Jogjakarta.

[8] Cho, B.T., Kang, S.K., Kim, M.S., Ryu, S.R., and An, D.K., 2006, Tetrahedron, 62, 8164 – 8168.

[9] Bush, H.J.S., 2003, The Preparation of 1,3,6,8-Tetraene Systems for Use as Intramolecular Diels-Alder Substrates in Desymmetrization Reactions, Ph.D. Thesis, University of Southampton, Southampton.

[10] Kusumaningsih, T., Sastrohamidjojo, H., and Soelistyowati, R.D., 2000, Teknosains, 13 (2), 247 – 261.

[11] Cacciatore, K.L., and Sevian, H., 2006, J. Chem. Educ. Supplementary Material, 83 (7), 1039 – 1040.



DOI: https://doi.org/10.22146/ijc.21611

Article Metrics

Abstract views : 2782 | views : 2622


Copyright (c) 2010 Indonesian Journal of Chemistry

Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

 

Indonesian Journal of Chemistry (ISSN 1411-9420 /e-ISSN 2460-1578) - Chemistry Department, Universitas Gadjah Mada, Indonesia.

Web Analytics View The Statistics of Indones. J. Chem.