Abstract
The response surface methodology using three-level Box–Behnken plans has been applied in order to optimize the yield of the cone and chair conformers in the synthesis of calix[4]resorcinol functionalized with 4-dimethylammoniophenyl group at the lower rim. We have used the data from single-factor experiments in which the temperature, reaction time, and molar ratio of HCl to the reactants of the reaction mixture have been varied to plot the response surfaces. The ratio of conformers has been calculated basing on the analysis of 1H NMR spectra of the products isolated from the reaction mixture. The adequacy of the proposed mathematical models for prediction of the yields of chair and cone conformers has been confirmed by high correlation coefficient (R 0.99979). The optimal conditions have been elaborated to maximize the yield of the chair (temperature 50°C, stirring duration 2 h, and molar ratio of HCl to reagents in the reaction mixture 1–1.5) and the cone conformations (68.6°С, 2.24–6.44 h, 2, respectively). The syntheses under the optimized conditions have afforded the yield of the chair and cone conformations of 100 and 57.70–58.07%, respectively.
This is a preview of subscription content, log in via an institution to check access.
REFERENCES
Shatalova, N.I., Gavrilova, E.L., Naumova, A.A., Krasil’nikova, E.A., Konovalov, A.I., Burilov, A.R., Foss, L.E., and Pudovik, M.A., Russ. J. Gen. Chem., 2005, vol. 75, no. 8, p. 1327. https://doi.org/10.1007/s11176-005-0419-3
Shatalova, N.I., Candidate Sci. (Chem.) Dissertation, Kazan, 2008.
Tunstad, L., Tucker, J., Dalcanale, E., and Weiser, J., J. Org. Chem., 1989, vol. 54, no. 6, p. 1305 https://doi.org/10.1021/jo00267a015
Miso, S., Adams, R.D., Guo, D.-S., and Zhang, Q.-F., J. Mol. Struct., 2003, vol. 659, p. 119 https://doi.org/10.1016/j.molstruc.2003.08.004
Guseva, E.V., Gavrilova, E.L., Naumova, A.A., Shatalova, N.I., Karimova, D.T., Polovnyak, V.K., and Morozov, V.I., Russ. J. Gen. Chem., 2008, vol. 78, no. 12, p. 2308. https://doi.org/10.1134/S1070363208120049
Guseva, E.V., Karimova, D.T., Polovnyak, V.K., Egorov, G.V., Gavrilova, E.L., Shatalova, N.I., Morozov, V.I., and Sokolova, A.V., Vestn. Kazan. Tekhnol. Univ., 2009, no. 5, p. 288.
Pashina, I.P., Candidate Sci. (Biol.) Dissertation, Moscow, 2013.
Khuri, A.I., Biom. Biostat. Int. J., 2017, vol. 5, no. 3, p. 87. https://doi.org/10.15406/bbij.2017.05.00133
Аdler, Yu.P., Markova, E.V., and Granovskii, Yu.V., Planirovanie pri poiske optimal’nykh uslovii (Planning in Search of Optimal Conditions), Moscow: Mir, 2004.
Box, G.E.P., Hunter, J.S., and Hunter, W.G., Statistics for Experimenters. Design, Innovation, and Discovery, New York: Wiley-Interscience, 2005.
Ferreira, S.L.C., Bruns, R.E., Ferreira, H.S., Matos, G.D., David, J.M., Brandao, G.C., Silva, E.G.P., Portugal, L.A., Reisc, P.S., Souza, A.S., and Santos, W., Analyt. Chim. Acta, 2007, vol. 597, p. 179. https://doi.org/10.1016/j.aca.2007.07.011
Bakeeva, R.F., Garmonov S.Yu, Vakhitova, O.E., and Sopin, V.F., J. Anal. Chem., 2022, vol. 77, no. 6, p. 686. https://doi.org/10.1134/S106193482206003X
Mohammadlou, M., Jafarizadeh-Malmiri, H., and Maghsoudi, H., Green Proc. Synth., 2017, vol. 6, p. 31. https://doi.org/10.1515/gps-2016-0075
Simões, A.,Veiga, F., Figueiras, A., and Vitorino, C.A., Int. J. Pharm., 2018, vol. 548, no. 1 P. 385. https://doi.org/10.1016/j.ijpharm.2018.06.052
Li, Q., Wang, Y., Li, Q., Foster, G., and Lei, C., RSC Adv., 2018, vol. 8, no. 16, p. 8770. https://doi.org/10.1039/c7ra13645e
Jiang, C., Sun, G., Zhou, Z., Lang, X., Pang, J., Li, Y., Zhang, X., Feng, C., Chen, X., Bao, Z., Sun, Q., Int. J. Biol. Macromol., 2019, vol. 121, p. 293. https://doi.org/10.1016/j.ijbiomac.2018.09.210
Agrawal, D., Shrivastava, Y., Singh, P.K., and De, S.K., J. Polymer Res., 2019, vol. 26, no. 7, p. 167. https://doi.org/10.1007/s10965-019-1825-2
Celebi, N., Yildiz, N., Calimli, A., and Demir, A.S., J. Supercr. Fluids, 2008, vol. 47, no. 2, p. 227. https://doi.org/10.1016/j.supflu.2008.07.022
Jourshabani, M., Badiei, A., Lashgari, N., and Ziarani, G.M., Chin. J. Catal., 2015, vol. 36, no. 11, p. 2020. https://doi.org/10.1016/S1872-2067(15)60898-1
Inger, M., Dobrzyńska-Inger, A., Rajewski, J., and Wilk, M., Catalysts, 2019, vol. 9, no. 3, p. 249. https://doi.org/10.3390/catal9030249
Pinheiro, D., Sunaja Devi, K.R., Jose, A., Karthik, K., Sugunan, S., and Krishna Mohan, M., J. Rare Earths, 2020, vol. 38, no. 11, p. 1171. https://doi.org/10.1016/j.jre.2019.10.001
Zhang, Y., Zhao, Q., Tang, H., Li, H., Li, D., Wang, Z., Gao, X., and Wang, F., Korean J. Chem. Eng., 2021, vol. 38, no. 5, p. 989. https://doi.org/10.1007/s11814-021-0757-9
Guolong, Y. and Lihui, Y., J. Oleo Sci., 2015, vol. 64, no. 6, p. 673. https://doi.org/10.5650/jos.ess14285
Sin, K.P., Basri, M., Rahman, M.B.A., Salleh, A.B., Rahman, R.N.Z.A., and Ariff, A., J. Oleo Sci., 2005, vol. 54, no. 10, p. 519. https://doi.org/10.5650/jos.54.519
Chaibakhsh, N., Abdul Rahman, M.B., Abd-Aziz, S., Basri M, Salleh, A.B., and Abdul Rahman, R.N.Z.R., J. Ind. Microbiol. Biotechnol., 2009, vol. 36, p. 1149. https://doi.org/10.1007/s10295-009-0596-x
Rosly, N.Z., Ishak, S., Abdullah, A.H., Alang Ahmad, S.A., Kamarudin, M.A., and Ashari, S.E., J. Saudi Chem. Soc., 2022, vol. 26, no. 1, p. 10140. https://doi.org/10.1016/j.jscs.2021.1014022
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
The authors declare that they have no conflicts of interest.
Rights and permissions
About this article
Cite this article
Bakeeva, R.F., Parfenova, A.G., Shatalova, N.I. et al. Optimization of Conditions for the Synthesis of Calix[4]resorcinol Conformers Containing 4-Dimethylammoniophenyl Fragments at the Lower Rim of the Molecule Based on the Response Surface Methodology Using Three-Level Box–Behnken Plans. Russ J Gen Chem 93, 310–320 (2023). https://doi.org/10.1134/S1070363223020111
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070363223020111