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Glycolic Acid‐Based Natural Deep Eutectic Solvents (NADESs) as Catalytic Reaction Media for the Synthesis of β‐Nitro Ketones

β‐nitro ketones represent highly significant compounds for their simultaneous nucleophilic and electrophilic reactive sites in 1,3‐related positions. These molecules are commonly obtained via nitration of enones in aprotic apolar organic… Click to show full abstract

β‐nitro ketones represent highly significant compounds for their simultaneous nucleophilic and electrophilic reactive sites in 1,3‐related positions. These molecules are commonly obtained via nitration of enones in aprotic apolar organic solvents (such as THF and CPME) with large excesses of nitrating agents and acetic acid. In this work the use of weakly acidic natural deep eutectic solvents (NADESs) – glycolic acid based‐ones – is proposed as both green and catalytic reaction media for the nitration of enones giving β‐nitro ketones. The NADESs mixtures employed were the ones formed by mixing glycolic acid with trimethylglycine, with choline chloride and with water. The reaction proceeded with stochiometric amounts of nitration agents and taking advantage from the catalytic behavior of the NADESs solvents; the scope was explored giving satisfactory yields.

Keywords: reaction; nitro ketones; glycolic acid; deep eutectic; eutectic solvents; natural deep

Journal Title: Asian Journal of Organic Chemistry
Year Published: 2025

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