Acetone → 6-(17-Carboxyheptadecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone

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Reaction Steps

In 10 ml of acetone is dissolved 172 mg of 6-(18-hydroxyoctadecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone (V:n=17). Separately, 2.672 g of chromic anhydride is dissolved in 2.3 ml of concentrated sulfuric acid and diluted with water to 10 ml. This diluted solution (0.5 ml) is added to the above acetone solution and the mixture is stirred under ice-cooling for 10 minutes. The reaction mixture is diluted with water and extracted with chloroform. The extract is washed with water and dried, and the solvent is distilled off under reduced pressure. The residue is column-chromatographed on silica gel, elution is carried out with chloroform and the eluate is recrystallized from ethanol. The above procedure yields 65 mg of 6-(17-carboxyheptadecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone (I:n=17, R=H) as orange-yellow crystals, m.p. 77°-79° C.

Provenance & Evidence