Cyclobutanone → Cyclopropanemethanol

Participants

Reaction Steps

The processes so far described for the oxidation of cyclobutanol to cyclobutanone use customary oxidizing agents in organic synthesis. A comparison of the existing oxidation methods is given in DE 199 10 464. In general, these are oxidations carried out in homogeneous systems from which the desired cyclobutanone first has to be isolated by extraction or the like. These processes generally lead to large amounts of waste and also to high burdens of toxic reagents, for example when using CrO3/oxalic acid according to Org. Synth. 1981, 60, 20–25. In this process, the direct oxidation of the solution of cyclobutanol in aqueous hydrochloric acid obtained from the isomerization of cyclopropylmethanol is described. For the conversion of 49.5 g of cyclopropylmethanol (results in 14–16 g of cyclobutanone, yield 31–35%), approximately 1.2 l of strongly acidic, chromium-containing wastewater is formed.

Provenance & Evidence