Acetone → Methyl 4,5-dimethoxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylate

HRID 374638Notes

Reaction equation

[OH:1][C:2]1[C:15]2[C:14](=[O:16])C3[C:8](=[CH:9][CH:10]=[CH:11]C=3O)[C:7](=[O:18])[C:6]=2[CH:5]=[C:4]([C:19]([OH:21])=O)[CH:3]=1.S([O:27][CH3:28])(OC)(=O)=O.[C:29](=O)([O-])[O-].[K+].[K+].CC(C)=O.O1[CH2:44][CH2:43][O:42][CH2:41]C1>>[CH3:29][O:1][C:2]1[C:15]2[C:14](=[O:16])[C:44]3[C:8](=[CH:9][CH:10]=[CH:11][C:43]=3[O:42][CH3:41])[C:7](=[O:18])[C:6]=2[CH:5]=[C:4]([C:19]([O:27][CH3:28])=[O:21])[CH:3]=1

Participants

Reactant 5

HCID 180Acetone

HCID 6497Dimethyl Sulfate

HCID 10168Rhein

HCID 11430Potassium Carbonate

HCID 312751,4-Dioxane

Product 1

HCID 11067354Methyl 4,5-dimethoxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylate

Procedure

A mixture of 9,10-dihydro-4,5-dihydroxy-9,10-dioxoanthracene-2-carboxylic acid (28.4 g), dimethyl sulphate (59 ml; 79 g) and anhydrous potassium carbonate (207 g) in `Drierire` dried acetone (1350 ml) and dioxan (1200 ml) was heated at reflux for 17 hours, with mechanical stirring. After allowing to cool, the suspension was filtered and the filter contents were washed with hot dioxan (5×50 ml).

Workup

temperaturewas heated
temperatureat reflux for 17 hours, with mechanical stirring
temperatureto cool
filtrationthe suspension was filtered
washthe filter contents were washed with hot dioxan (5×50 ml)

Sources & evidence

ORD record: ord-d732113203ea46d5ab373a7aa0edeabf
Source dataset: uspto-grants-1996_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05480873

Reaction notes

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