Fries rearrangement

The Fries rearrangement is a chemical reaction that involves the conversion of phenolic esters or lactams into hydroxyaryl ketones through the use of a Lewis acid catalyst. This process typically requires long reflux times or photochemical conditions. The Fries rearrangement is a versatile method for producing ortho- or para-hydroxyphenyl ketones.From: Clay Mineral Catalysis of Organic Reactions [2018], Microwave-Assisted Organic Synthesis [2019], Advances in Microwave Chemistry [2018]

Selectivities in the Microwave-Assisted Organic Reactions

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Published in Banik Bimal Krishna, Bandyopadhyay Debasish, Advances in Microwave Chemistry, 2018

Jiaxi Xu

The Fries rearrangement is a general method to prepare ortho- or para-hydroxyphenyl ketones. The Fries rearrangement of phenyl acetate shows different regioselectivity under the catalysis of either aluminum trichloride or zinc powder under conventional heating or microwave irradiation, even reverse the regioselectivity under the catalysis of aluminum trichloride (Scheme 6.12) [19, 20].

Laterally substituted biphenyl benzoates ‒ synthesis and mesomorphic properties

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Published in Liquid Crystals, 2021

Martin Cigl, František Hampl, Jiří Svoboda, Natalia Podoliak, Sergei Stulov, Michal Kohout, Vladimíra Novotná

Ortho-halogenated 4-(alkoxy)benzoic acids 5/n and 6/n were prepared by a multistep procedure from the corresponding meta-halogenated phenols 7a,b. In the initial step, the phenols 7a,b were O-acetylated and then underwent the Fries rearrangement to acetophenones 8a,b by aluminium chloride catalysis. In the next step, the hydroxy group of acetophenones 8a,b was alkylated with alkyl bromides (n = 6,8,10,12) yielding the corresponding 4-(alkoxy)acetophenones 9/n and 10/n. In the last step, the acetophenones were transformed to the corresponding benzoic acids 5/n and 6/n using the haloform reaction, respectively.

Fries rearrangement

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Selectivities in the Microwave-Assisted Organic Reactions

Laterally substituted biphenyl benzoates ‒ synthesis and mesomorphic properties