Oxalic Acid → 4-Demethyl Daunomycinone

Participants

Reaction Steps

To a refluxed solution of 10 g. of daunomycinone (II) in 1 liter of dichloromethane, 30 g. of aluminum trichloride were added over a two hour period with stirring. After an additional 4 hour period, the reaction mixture was cooled and poured into ice water containing 150 g. of oxalic acid. The organic layer was separated, washed with water and concentrated in vacuo to yield 6 g. of crystalline 4-demethoxy-4-hydroxy-daunomycinone (III), which were collected by filtration.

Provenance & Evidence