Acetic Acid → HCID 54544855, compound

HRID 1976928Notes

Reaction equation

HRID 1976928 reaction equation
[C:1]([O:4][C:5]1[C:18]2[C:17](=[O:19])[C:16]3[C:11](=[CH:12]C(C)=[CH:14][CH:15]=3)[C:10](=[O:21])[C:9]=2[CH:8]=[C:7]([O:22][C:23](=[O:25])[CH3:24])[CH:6]=1)(=O)[CH3:2].[OH2:26].[C:27]([OH:30])(=[O:29])[CH3:28]>C(OC(=O)C)(=O)C>[C:1]([O:4][C:5]1[C:18]2[C:17](=[O:19])[C:16]3[C:11](=[CH:12][C:28]([C:27]([OH:30])=[O:29])=[CH:14][CH:15]=3)[C:10](=[O:21])[C:9]=2[CH:8]=[C:7]([O:22][C:23](=[O:25])[CH3:24])[CH:6]=1)(=[O:26])[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic Acid2×HCID 962WaterHCID 12634030HCID 12634030, compound

Product 1

HCID 54544855HCID 54544855, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

2.2 1, 3-Diacetoxy-6-methyl-anthraquinone (20 mg) (obtained in Example 2.1) was dissolved in a 1:1 mixture of acetic anhydride and acetic acid (16.6 ml) at 50° C. and added dropwise to a solution of CrO3 (135 mg) in aqueous 40% acetic acid (2.7 ml). The reaction mixture was then stirred for three hours, cooled and poured into 200 ml of water. After being left for two hours, the solution was extracted with ethyl acetate, washed with water and then extracted twice with saturated sodium bicarbonate solution. The aqueous phase was washed twice with methylene chloride, acidified with dilute HCl and extracted with ethyl acetate. The organic extract was evaporated to dryness yielding 18 mg of 1,3-diacetoxy-6-carboxy-anthraquinone (IV). UV-vis (EtOH) λmax353, 483, 530 sh, 564 nm (ε 22000, 30000, 20000, 15000)

Workup

  1. temperaturecooled
  2. waitAfter being left for two hours
  3. extractionthe solution was extracted with ethyl acetate
  4. washwashed with water
  5. extractionextracted twice with saturated sodium bicarbonate solution
  6. washThe aqueous phase was washed twice with methylene chloride
  7. extractionextracted with ethyl acetate
  8. extractionThe organic extract
  9. customwas evaporated to dryness

Sources & evidence

ORD record
ord-4667162691fc4736b3f2e8340db49d86
Source dataset
uspto-grants-2001_05
Patent number
US06229048B1

Reaction notes

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