Oxygen → 6-(22-Hydroxydocosyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone

Participants

Reaction Steps

In dimethylformamide (200 ml) are suspended 6-(22-hydroxydocosyl)-2,3-dimethoxy-5-methyl phenol (300 mg) and bis(4-hydroxysalicylidene)ethylenediiminocobalt(II) (50 mg). The suspension is stirred in an oxygen gas stream at ambient temperature and atmospheric pressure for 7 days. The insoluble matter is filtered off and the filtrate is concentrated under reduced pressure. The residue is diluted with water and extracted with ethyl acetate. The extract is treated in a conventional manner and the product is chromatographed on a silica gel column. The fractions obtained by elution with chloroform are pooled and recrystallized from ethanol to give orange-yellow needles of 6-(22-hydroxydocosyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone (I, n=22). m.p. 89°-90.5° C.

Provenance & Evidence