One-Step Oxidation of 2-Arylpropanols to 2-Arylpropionic Acids: Improving Sustainability in the Synthesis of Profens

Abstract

Three oxidation procedures were evaluated for the synthesis of optically pure 2-arylpropionic acids. Efficient, mild, and eco-friendly conditions were obtained with the system comprising TEMPO, NaClO, and NaClO₂. Thus a series of profens were obtained in good to excellent yields.

Key words

oxidation - alcohols - carboxylic acids - anti-inflammatory agents - profens - TEMPO

References and Notes

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9

Compounds 1b-g were obtained by BH₃˙SMe₂ reduction from commercially available racemic acids. Compound 1h was easily obtained in a three steps synthesis starting from ketoprofen (EtOH, BF₃˙OEt₂ cat.; ethylene glycol, TsOH cat. in toluene; LiAlH₄ in THF).

15

Referred to reported data, see ref. 7.