Studies into the direct oxidation of codeinone to 14-hydroxycodeinone

Article abstract of DOI:10.1016/S0040-4020(99)00665-1

The direct oxidation of codeinone (5) to 14-hydroxycodeinone (6) was investigated with a wide range of oxidizing agents. The majority of reagents gave little or no desired product. Peracids were found to be moderately successful, with dimethyl peracetic acid giving the greatest yield (37%). Metallic oxidants generally gave rise to competing oxidations, however Co(AcO)₃ was found to conveniently oxidize 5 to 6 in 51% yield, representing a practical, non-chromatographic procedure for the preparation of 14- hydroxycodeinone.