Trioxide in Acetone Jones Oxidation

Chromium Trioxide in Acetone Jones Oxidation. Organic solvents other than acetic acid can be used with aqueous chromium trioxide. Jones used acetone as a cosolvent in a dilute sulfuric acid solution, and found that oxidation of alkynyl carbinols was improved when compared to other known procedures. Secondary alcohols can be oxidized to ketones, and primary alcohols can be oxidized to either an aldehyde or a carboxylic acid. An example is the oxidation of 18 to give ketone 19 in 94% yield, taken from 

Ando s synthesis of hymenolin. xhis chromium trioxide/acetone/sulfuric acid reagent is often referred to as the Jones reagent, and oxidation of alcohols with this reagent is called Jones oxidation. Direct conversion of a primary alcohol to an acid is seen in the oxidation of 20 to 21, quantitatively, in Omura, Smith and coworker s synthesis of (+)-lactacystin.5 Jones oxidation is especially useful for molecules that contain alkenyl or alkynyl groups. 2 Oxidation of alcohols is usually faster in acetone than in acetic acid, and using a large excess of acetone protects the ketone product from further oxidation. - Many primary alcohols are oxidized 

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