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Academic Journal of Materials & Chemistry, 2023, 4(4); doi: 10.25236/AJMC.2023.040407.

Williamson Ether Synthesis: O-Alkylation Reaction Using Halogenated Hydrocarbons as Alkylating Agents

Author(s)

Honggao Duan

Corresponding Author:
Honggao Duan
Affiliation(s)

School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Benxi, Liaoning, 117004, China

Abstract

The Williamson synthesis method is a method for preparing asymmetric ethers, which is obtained by the reaction of halogenated hydrocarbons with sodium alcohol or sodium phenol. According to literature research, the influencing factors of this reaction include halogenated hydrocarbons, alkylated alcohols, catalysts, solvents, and side reactions; In addition, this method can be used to introduce various substituents such as saturated, unsaturated, aliphatic, and aromatic hydrocarbon groups in drug synthesis, thereby obtaining a variety of pharmaceutical intermediates or drugs. This article selects the antitumor drug gefitinib involved in this reaction as a case study to illustrate the complete synthesis route of this drug. Other reaction types and names involved in the drug synthesis route are also described.

Keywords

Williamson ether synthesis method; influencing factors; application of drug synthesis; synthesis route; route exploration and analysis

Cite This Paper

Honggao Duan. Williamson Ether Synthesis: O-Alkylation Reaction Using Halogenated Hydrocarbons as Alkylating Agents. Academic Journal of Materials & Chemistry (2023) Vol. 4, Issue 4: 41-45. https://doi.org/10.25236/AJMC.2023.040407.

References

[1] Science; New Findings from Zhejiang Sci-Tech University Yields New Data on Science (Cotton Fabric-Supported Cationic Acrylate Polymer as an Efficient and Recyclable Catalyst for Williamson Ether Synthesis Reaction in Solid-Liquid-Liquid Phase Transfer ...) [J]. Chemicals & Chemistry, 2020.

[2] Peng Hui, Lei Manjun, Yang Lihui, Sun Jie, Yang Lei, Zhao Qiangqiang. Cotton Fabric-Supported Cationic Acrylate Polymer as an Efficient and Recyclable Catalyst for Williamson Ether Synthesis Reaction in Solid-Liquid-Liquid Phase Transfer Catalysis System.[J]. ACS omega, 2020, 5(34).

[3] Long Yuyang, Jin Zhiyuan, Li Lijun, Zhang Mingxin, Hu Lifang, Shen Dongsheng, Ruan Jinmu. Dechlorination of chlorotoluene rectification residual liquid (CRRL) by using Williamson ether synthesis (WES) method.[J]. Environmental science and pollution research international, 2020, 27(12).

[4] Baar Marsha R. Research Experience for the Organic Chemistry Laboratory: A Student-Centered Optimization of a Microwave-Enhanced Williamson Ether Synthesis and GC Analysis[J]. Journal of Chemical Education, 2018, 95(7).

[5] Surfactants and Detergents. Findings from University of Burdwan Reveals New Findings on Surfactants and Detergents [Green Methodology Development for the Surfactant Assisted Williamson Synthesis of 4-benzyloxy Benzoic Acid (Ether) In Aqueous Media] [J]. Chemicals & Chemistry, 2020.

[6] Sangita Mandal, Satyajit Biswas, Monohar Hossain Mondal, Bidyut Saha. Green Methodology Development for the Surfactant Assisted Williamson Synthesis of 4-Benzyloxy Benzoic Acid (Ether) in Aqueous Media [J]. Tenside Surfactants Detergents, 2020, 57(2).

[7] Baranová Zuzana, Amini Hashem, Neupane Madhav, Garrett Sydney C., Ehnbom Andreas, Bhuvanesh Nattamai, Reibenspies Joseph H., Gladysz John A.. Syntheses, Structural Studies, and Copper Iodide Complexes of Macrocycles Derived from Williamson Ether Syntheses Involving 2, 9-Bis (4-hydroxyphenyl)-1, 10-phenanthroline, α, ω-Dibromides, and Resorcinol or 2, 7- Dihydroxynaphthalene [J]. Australian Journal of Chemistry, 2017, 70(4).

[8] Kazutaka Shibatomi, Manato Kotozaki, Nozomi Sasaki, Ikuhide Fujisawa, Seiji Iwasa. ChemInform Abstract: Williamson Ether Synthesis with Phenols at a Tertiary Stereogenic Carbon: Formal Enantioselective Phenoxylation of β‐Keto Esters.[J]. ChemInform, 2016, 47(8).

[9] Shibatomi Kazutaka, Kotozaki Manato, Sasaki Nozomi, Fujisawa Ikuhide, Iwasa Seiji. Williamson Ether Synthesis with Phenols at a Tertiary Stereogenic Carbon: Formal Enantioselective Phenoxylation of β-Keto Esters.[J]. Chemistry (Weinheim a der Bergstrasse, Germany), 2015, 21(40).

[10] Steffen Hallmann, Mark J. Fink, Brian S. Mitchell. Williamson ether synthesis: an efficient one-step route for surface modifications of silicon nanoparticles[J]. Journal of Experimental Nanoscience, 2015, 10(8).