European Journal of Chemistry 2014, 5(3), 513-516. doi:10.5155/eurjchem.5.3.513-516.1086

A study of coupling reaction to synthesize diphenylmethane derivatives


Huma Aslam Bhatti (1,*) , Qurat-Ul-Ain Zaheer (2) , Memoona Khatoon (3) , Mark Edward Light (4) , Abdul Hameed (5)

(1) Husein Ebrahim Jamal Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi, 75270, Pakistan
(2) Husein Ebrahim Jamal Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi, 75270, Pakistan
(3) Husein Ebrahim Jamal Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi, 75270, Pakistan
(4) School of Chemistry, University of Southampton, Highfield, Southampton, SO17 1BJ, England
(5) Husein Ebrahim Jamal Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi, 75270, Pakistan
(*) Corresponding Author

Received: 28 Apr 2014, Accepted: 01 Jun 2014, Published: 30 Sep 2014

Abstract


The class of compounds having diphenylmethane framework occupy a distinct place in natural bioactive compounds and also serve as useful intermediates in various commercially important synthetic molecules. Conventionally, Friedel-Craft type reactions were used to synthesize such diphenylmethane derivatives. However, herein we report a unique approach in which, two benzyl alcohol molecules were coupled in the presence of different halogenating agents (SOCl2, PBr3 and MeSO2Cl) to afford the desired diphenylmethane derivative, bis(2,4-bis(benzyloxy)-5-methoxyphenyl)methane. It has been found that the coupling reaction is strongly influenced by the electronic effects and number of the substituents on the phenyl ring. The resultant compound, bis(2,4-bis(benzyloxy)-5-methoxyphenyl)methane, was obtained in excellent yield (83-85%) and completely characterize with different spectroscopic techniques.


Keywords


Benzyl alcohol; Thionyl chloride; Coupling reaction; Halogenating agents; Phosphorus tribromide; Diphenylmethane derivative

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DOI: 10.5155/eurjchem.5.3.513-516.1086

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How to cite


Bhatti, H.; Zaheer, Q.; Khatoon, M.; Light, M.; Hameed, A. Eur. J. Chem. 2014, 5(3), 513-516. doi:10.5155/eurjchem.5.3.513-516.1086
Bhatti, H.; Zaheer, Q.; Khatoon, M.; Light, M.; Hameed, A. A study of coupling reaction to synthesize diphenylmethane derivatives. Eur. J. Chem. 2014, 5(3), 513-516. doi:10.5155/eurjchem.5.3.513-516.1086
Bhatti, H., Zaheer, Q., Khatoon, M., Light, M., & Hameed, A. (2014). A study of coupling reaction to synthesize diphenylmethane derivatives. European Journal of Chemistry, 5(3), 513-516. doi:10.5155/eurjchem.5.3.513-516.1086
Bhatti, Huma, Qurat-Ul-Ain Zaheer, Memoona Khatoon, Mark Edward Light, & Abdul Hameed. "A study of coupling reaction to synthesize diphenylmethane derivatives." European Journal of Chemistry [Online], 5.3 (2014): 513-516. Web. 16 Sep. 2019
Bhatti, Huma, Zaheer, Qurat-Ul-Ain, Khatoon, Memoona, Light, Mark, AND Hameed, Abdul. "A study of coupling reaction to synthesize diphenylmethane derivatives" European Journal of Chemistry [Online], Volume 5 Number 3 (30 September 2014)

DOI Link: https://doi.org/10.5155/eurjchem.5.3.513-516.1086

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