Oxygen → Idebenone

Participants

Reaction Steps

To a dichloromethane solution (30 ml) of 6-(10-hydroxydecyl)-2,3-dimethoxy-5-methylphenol (1.4 g) is added bis(salicylidene)ethylenediiminocobalt(II) (0.06 g), and the mixture is stirred in oxygen streams at 20° C. and atmospheric pressure for 72 hours. After the reaction has been completed, the reaction mixture is passed through a bed of a small quantity of silica gel (about 15 g) to remove the catalyst. The solvent is then distilled off and the residue is recrystallized from ether-hexane (1:4). The above procedure yields 6-(10-hydroxydecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone (1.01 g) as orange-yellow needles melting at 51° C.-52° C.

Provenance & Evidence