External Catalyst‐Free Oxidation of Benzyl Halides to Benzoic Acids Using NaOH/TBHP in Water. Issue 9 (4th August 2021)

• Record Type: Journal Article
• Authors: Saini, Parul; Krishnan, Anandhu; Yadav, Deepak; Hazra, Susanta; Elias, Anil J.
• Is Part Of: Asian journal of organic chemistry. Volume 10:Issue 9(2021)
• Page Start: 2355
• Page End: 2359
• Publication Date: 2021-08-04
• Subjects: Aqueous medium -- Carboxylic acids -- External catalyst free -- Metal-free -- Oxidation; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.202100390
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: An efficient and metal‐free methodology for the oxidation of benzyl halides to benzoic acids using an inexpensive and green oxidant (TBHP) in aqueous basic medium has been developed. This protocol offers an excellent way to avoid adding catalysts and involves the use of an in‐situ generated halide ion as catalyst. It is also the first report on the oxidation of benzyl iodides to benzoic acids. A series of carboxylic acids were prepared from benzyl halides in high yields under mild reaction conditions by this method which does not require chromatographic purification. Gram scale reactions for the synthesis of the carboxylic acids in good yields have been successfully carried out using benzyl chloride, bromide and iodide. As an industrial application, the synthesis of a key monomer used for the synthesis of polyethylene terephthalate (PET), i. e., terephthalic acid (PTA), has also been accomplished in good yields. Abstract : External catalyst‐free oxidation of benzyl halides to benzoic acids was achieved using NaOH/TBHP in water medium. This simple and greener one‐pot synthesis has produced good yields of benzoic acids when TBHP was used as oxidant and water as solvent under mild reaction conditions. Terephthalic acid (PTA) was also synthesised by this method in good yields.