Acetone → 2,6-dimethoxyanthraquinone

HRID 1440437Notes

Reaction equation

HRID 1440437 reaction equation
[OH:1][C:2]1[CH:15]=[CH:14][C:13]2[C:12](=[O:16])[C:11]3[C:6](=[CH:7][CH:8]=[C:9](O)[CH:10]=3)C(=O)[C:4]=2[CH:3]=1.[C:19](=[O:22])([O-])[O-].[K+].[K+].S([O:30][CH3:31])(OC)(=O)=O.O.[CH3:33]C(C)=O>>[CH3:33][O:1][C:2]1[CH:15]=[CH:14][C:13]2[C:12](=[O:16])[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([O:30][CH3:31])[CH:10]=3)[C:19](=[O:22])[C:4]=2[CH:3]=1

Participants

6

Reactant 5

HCID 180AcetoneHCID 962WaterHCID 6497Dimethyl SulfateHCID 67762,6-DihydroxyanthraquinoneHCID 11430Potassium Carbonate

Product 1

HCID 45899982,6-dimethoxyanthraquinone

Procedure

To a suspension of 2,6-dihydroxyanthraquinone (3 g, 12.5 mmole) and anhydrous potassium carbonate (23 g) in acetone (400 ml), dimethyl sulfate (20 g, 158 mmole) was added at room temperature. The resulting mixture was reacted with stirring for 6 hours under reflux. After standing at room temperature overnight, the reaction mixture was poured into cold H2O (580 ml). The precipitate was filtered and dried. The resultant crude dark brown solid (3.1 g) was recrystallized from benzene to give 2.7 g of 2,6-dimethoxyanthraquinone as yellow-brown crystals.

Workup

  1. additionwas added at room temperature
  2. customThe resulting mixture was reacted
  3. temperatureunder reflux
  4. waitAfter standing at room temperature overnight
  5. filtrationThe precipitate was filtered
  6. customdried
  7. customThe resultant crude dark brown solid (3.1 g) was recrystallized from benzene

Sources & evidence

ORD record
ord-ce2fc24b4bbc476e947e03133d9e7394
Source dataset
uspto-grants-1996_03
Patent number
US05498748

Reaction notes

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