3-Methyl-1-(propyloxycarbonylmethyl)imidazolium octylsulfate 1a and 3-methyl-1-(pentyloxycarbonylmethyl)imidazolium octylsulfate 2a are ionic liquids that have previously been shown to be readily biodegradable in the CO2 headspace test (ISO 14593). In the present study, these ionic liquids were evaluated as reaction media for Diels–Alder and hydrogenation reactions. The comparison of the performance of these two designer solvents in these reactions with those conducted in other, non-biodegradable ionic liquids has demonstrated that they are comparable and viable solvents.