Sulfuric Acid → Anthraquinone-2-aldehyde diacetate

HRID 1610782Notes

Reaction equation

[CH3:1][C:2]1[CH:15]=[CH:14][C:13]2[C:12](=[O:16])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[O:17])[C:4]=2[CH:3]=1.S(=O)(=O)(O)[OH:19]>C(O)(=O)C.C(OC(=O)C)(=O)C.[O-2].[O-2].[O-2].[Cr+6]>[C:12]([OH:16])(=[O:19])[CH3:13].[C:12]([OH:16])(=[O:19])[CH3:13].[CH:3]1[C:4]2[C:5](=[O:17])[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:12](=[O:16])[C:13]=2[CH:14]=[CH:15][C:2]=1[CH:1]=[O:19]

Participants

Conditions

Temperature: 5 °C

Procedure

To a solution of 2-methylanthraquinone (16.0 g, 72.0 mmol) in a mixture of acetic acid (400 ml) and acetic anhydride (400 ml) was added concentrated sulfuric acid (16 ml) at 5° C. Chromium trioxide (18.0 g, 0.18 mmol) was added over a period of 1 hour at 5° C. The reaction mixture was then stirred at 5° C. for 4 hours, poured into ice water, and extracted with chloroform. The organic extract was dried over MgSO4 and concentrated under vacuum to give anthraquinone-2-aldehyde diacetate (16.0 g, 65%.) To a solution of the anthraquinone-2-aldehyde diacetate (16.0 g, 47.3 mmol) in acetic acid (400 ml) was added dropwise 35% aqueous hydrochloric acid (170 ml) at room temperature. The reaction mixture had been stirred while refluxing for 15 min, cooled to room temperature, filtered off with suction, and washed with water. After drying, anthraquinone-2-aldehyde (10.0 g, 89%) was obtained.

Workup

extractionextracted with chloroform
extractionThe organic extract
dry with materialwas dried over MgSO4
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-4dacee892c4049e9beae61b6f0d1e181
Source dataset: uspto-grants-2006_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06984462B2

Reaction notes

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