Synthesis of 1-(2-Methoxybenzyl)-1,10-phenanthrolin-1-ium Bromide from Gandapura Oil
Muhammad Idham Darussalam Mardjan, Dhina Fitriastuti, Bambang Purwono, Jumina Jumina
J. Pure App. Chem. Res. Vol 8, No 3 (2019), pp. 239-244
Submitted: June 15, 2019     Accepted: December 10, 2019     Published: December 12, 2019
DOI: http://dx.doi.org/10.21776/ub.jpacr.2019.008.03.484

Abstract


Cover Image

This study describes simple synthetic method to prepare 1-(2-methoxybenzyl)-1,10-phenanthrolin-1-ium bromide from gandapura oil. The salt were synthesized in four steps. Initially, commercial gandapura oil was directly subjected to the alkylation reaction under basic condition using dimethyl sulfate to give methyl 2-methxybenzoate in 86% yield. Next, the produced benzoate ester was reduced by LiAlH4 to produce 2-methoxybenzyl alcohol in 67% yield. The treatment of benzyl alcohol with phosphorus tribromide under solvent free condition produced the corresponding benzyl bromide (in 67% yield), which was directly introduced into bimolecular nucleophilic substitution reaction with 1,10-phenantroline monohydrate to finally give the desired product in 63% yield.


Keywords : phenanthroline salt, gandapura oil, alkylation, reduction, halogenation and bimolecular nucleophilic substitution.
Full Text: PDF


References


[1]. Antakli, S., Sarkis, N., Kabaweh, M., Asian J. Chem., 2010, 22 (6), 4931–4938.

[2]. Bencini, A. and Lippolis, V., Coord. Chem. Rev. 2010, 254 (17–18), 2096–2180.

[3]. Aboul-Gheit, A. K., Ahmed, S. M., El-Desouki, D. S., Abdel-Azeem, S. M., El-Shahat, M. F., Eur. J. Chem. 2011, 2 (1), 104–108.

[4]. Abebe, A. and Hailemariam, T., Bioinorg. Chem. Appl., 2016, 3607924.

[5]. Yapi, A.D., Valentin, A., Chezal, J.M., Chavignon, O., Chaillot, B., Gerhardt, R., Teulade, J.C., Blache, Y., Arch. Pharm., 2006, 339 (4), 201–206.

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

[7]. Firdaus, M., Jumina, J., & Anwar, C., Indones. J. Chem., 2008, 8 (3), 423–425.

[8]. Hadanu, R., Matsjeh, S., Jumina, J., Mustofa, M., Widjayanti, M. A., & Solikhah, E. N., Indones. J. Chem. 2010, 7 (2), 197–201.

[9]. Hadanu, R., Matsjeh, S., Jumina, J., Mustofa, M., Solikhah, E. N., Widjayanti, M. A., Indones. J. Chem., 2012, 12 (2), 152–162.

[10]. Fitriastuti, D., Mardjan, M. I. D., Jumina, J., & Mustofa, M., Indones. J. Chem., 2014, 14 (1), 1–6.

[11]. Hadanu, R., Anwar, C., Jumina, J., Tahir, I., & Mustofa, M., Indones. J. Chem. 2014, 4 (2), 82–97.

[12]. Hadanu, R., Mustofa, M. & Nazudin, N., MAKARA J. Sci., 2012, 16(2), 101-109.

[13]. Wijayanti, M.A., Sholikhah, E.N., Hadanu, R., Jumina, J., Supargiyono, S., & Mustofa, M., Malar. Res. Treat., 2010, 540786.

[14]. Widjayanti, M. A., Solikhah, E. N., Tahir, I., Hadanu, R., Jumina, J., Supargiyono, S. & Mustofa, M., J. Health Sci., 2006, 52 (6), 794–799.

[15]. Solikhah, E. N., Supargiyono, S., Jumina, J., Widjayanti, M. A., Tahir, I., Hadanu, R. & Mustofa, M., Southeast Asian J. Trop. Med. Public Health, 2006, 37(6), 1072–1077.

[16]. Li, H. and Yan, C.G., Tetrahedron, 2011, 67(16), 2863–2869.


Refbacks

  • There are currently no refbacks.


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