Hydrochloric Acid → 1-Hydroxy-9,10-dioxo-9,10-dihydroanthracen-2-yl acetate

HRID 229320

Reaction equation

HRID 229320 reaction equation
[CH:1]1[CH:6]=[C:5]2[C:7]([C:9]3[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([OH:18])[C:10]=3[C:11](=[O:12])[C:4]2=[CH:3][CH:2]=1)=[O:8].[C:19](OC(=O)C)(=[O:21])[CH3:20].Cl>N1C=CC=CC=1>[CH3:20][C:19]([O:17][C:14]1[CH:15]=[CH:16][C:9]2[C:7](=[O:8])[C:5]3[CH:6]=[CH:1][CH:2]=[CH:3][C:4]=3[C:11](=[O:12])[C:10]=2[C:13]=1[OH:18])=[O:21]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6293AlizarinHCID 7918Acetic Anhydride

Product 1

HCID 155209421-Hydroxy-9,10-dioxo-9,10-dihydroanthracen-2-yl acetate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

This substrate was prepared using a method familiar to those skilled in the art. Two grams of Alizarin were dissolved in 5 ml of Pyridine and treated with a mixture of 2.5 ml of Acetic anhydride and 5 ml of Pyridine. After 16 hours at room temperature, the yellow solution was poured into 100 ml of hydrochloric acid containing ice. The precipitated Acetate was recovered by filtration with aspiration and then washed in water. Recrystallization from Acetone yielded 1.4 g of Alizarin-2-acetate in the form of yellow crystals.

Workup

  1. customThis substrate was prepared
  2. additioncontaining ice
  3. filtrationThe precipitated Acetate was recovered by filtration with aspiration
  4. washwashed in water
  5. customRecrystallization from Acetone

Sources & evidence

ORD record
ord-ae12f970bfe34ad88172f73135b7942c
Source dataset
uspto-grants-2009_07
Patent number
US07563592B2

Linked notes

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