Acetic Acid → HCID 50923868, compound

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Reaction Steps

FIG. 2 represents chemical structures, reaction schemes and reaction yields for an example of an oxidation of the substrate 4-methylcyclohexyl pivalate in the presence of two different complexes. Experimental details are provided in Examples 3 and 4. Reaction of the substrate with complex 4 in the presence of acetic acid (AcOH) yielded 38% (by GC) of the mono-oxidized product 4-hydroxy-4-methylcyclohexyl pivalate (entry 4). This yield was amplified by using a three-fold reagent addition procedure, in which each addition of the complex included 5 mol % complex 4 and 0.5 equivalent AcOH, and each addition of oxidant included 1.2 equivalents H2O2. The three-fold reagent addition procedure was carried out over a period of 30 minutes, providing diastereomerically pure hydroxylated product 2 in 51% isolated yield (entry 5).

Provenance & Evidence