Hydrochloric Acid → HCID 12824129, compound

Participants

Reaction Steps

Lithium aluminum hydride (740 mg) is suspended in 80 ml of dried ether, and a solution of 1.06 g of 2,3-dimethoxy-6-(12-methoxycarbonyldodecyl)-5-methyl-1,4-benzoquinone in 100 ml of dried ether is added dropwise with stirring and ice cooling. After 1.5 hours, ice water is added so as to decompose the excess lithium aluminum hydride, then acidified with hydrochloric acid and extracted with ether. The extract is washed with water and concentrated under reduced pressure. The residue is dissolved in 30 ml of methanol, a solution of 12 g of ferric chloride in 60 ml of water is added, and the mixture is stirred at room temperature for 1.5 hours. The liquid reaction mixture is diluted with water and extracted with ethyl acetate. The extract is washed with water and dried, and the solvent is distilled off under reduced pressure. The residue is dissolved in chloroform and subjected to silica gel column chromatography. The crystals recovered from the chloroform-ethanol (99:1) eluate are recrystallized from ether-hexane to give 727 mg of 6-(13-hydroxytridecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone (in formula I, n=13) as yellow needles. m.p. 65°-66° C.

Provenance & Evidence