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26.1.1.2.2.3 Variation 3: With Chromic Acid in Acetone

DOI: 10.1055/sos-SD-026-00003

von Angerer, S.Science of Synthesis, (20052646.

An alternative solvent, which is widely used for oxidations with chromic acid, is acetone. This oxidizing system has been termed the Jones reagent[‌65‌] and its use as an oxidizing agent is a standard procedure in organic syntheses. Generally a solution of chromic acid in dilute sulfuric acid is added to a solution of the secondary alcohol in acetone. The dilution of the chromic acid in the course of the reaction minimizes overoxidation. Excess oxidizing agent can be destroyed with propan-2-ol.[‌66‌] By this method it is possible to oxidize secondary hydroxy groups next to triple bonds, e.g. the formation of oct-3-yn-2-one (21) (Scheme 14).[‌67‌,‌68‌] Examples of ketones formed using this reagent are pent-3-yn-2-one (70%),[‌69‌] hex-1-yn-3-one (72%),[‌65‌] and 1-chloropent-1-yn-3-one (83%).[‌69‌,‌70‌]

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