Oxalic Acid → 4-Demethyl Daunomycinone

HRID 1448939Notes

Reaction equation

HRID 1448939 reaction equation
[CH3:1][C:2]([C@@:4]1([OH:29])[CH2:27][C@H:26]([OH:28])[C:7]2=[C:8]([OH:25])[C:9]3[C:21](=[O:22])[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][C:19]=4[O:23]C)[C:13](=[O:14])[C:10]=3[C:11]([OH:12])=[C:6]2[CH2:5]1)=[O:3].[Cl-].[Cl-].[Cl-].[Al+3].C(O)(=O)C(O)=O>ClCCl>[CH3:1][C:2]([C@:4]1([OH:29])[CH2:5][C:6]2[C:7](=[C:8]([OH:25])[C:9]3[C:21](=[O:22])[C:20]4[C:19]([OH:23])=[CH:18][CH:17]=[CH:16][C:15]=4[C:13](=[O:14])[C:10]=3[C:11]=2[OH:12])[C@@H:26]([OH:28])[CH2:27]1)=[O:3]

Participants

5

Reactant 3

HCID 971Oxalic AcidHCID 83843(+)-DaunomycinoneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 1711974-Demethyl Daunomycinone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  1. temperaturethe reaction mixture was cooled
  2. customThe organic layer was separated
  3. washwashed with water
  4. concentrationconcentrated in vacuo
  5. customto yield 6 g
  6. filtrationof crystalline 4-demethoxy-4-hydroxy-daunomycinone (III), which were collected by filtration

Sources & evidence

ORD record
ord-70c52c294bd94236b04860348d58da93
Source dataset
uspto-grants-1980_02
Patent number
US04188377

Reaction notes

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