Pyridine → 4,5-Bisbutyryloxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid

HRID 12939Notes

Reaction equation

HRID 12939 reaction equation
[OH:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][C:12]=3[OH:17])[C:7](=[O:18])[C:6]=2[CH:5]=[C:4]([C:19]([OH:21])=[O:20])[CH:3]=1.[C:22](Cl)(=[O:26])[CH2:23][CH2:24][CH3:25].C([O:31][CH2:32][CH3:33])(=O)C.ClCCl.N1C=CC=[CH:39][CH:38]=1>O>[C:22]([O:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][C:12]=3[O:17][C:32](=[O:31])[CH2:33][CH2:38][CH3:39])[C:7](=[O:18])[C:6]=2[CH:5]=[C:4]([C:19]([OH:21])=[O:20])[CH:3]=1)(=[O:26])[CH2:23][CH2:24][CH3:25]

Participants

7

Reactant 5

HCID 1049PyridineHCID 6344DichloromethaneHCID 8855Butyryl chlorideHCID 8857Ethyl AcetateHCID 10168Rhein

Product 1

HCID 112931694,5-Bisbutyryloxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acidYield 45%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4,5-Dihydroxy-9,10-dioxoanthracene-2-carboxylic acid (3.0 g) was suspended in pyridine (100 ml) and stirred at RT for 30 mins. Butyryl chloride was added (3.6 g, 5 equiv.) to give a clear reaction mixture which was stirred at RT over the weekend. The reaction mixture was reduced to a smaller volume and quenched with 2M HCl (200 ml), adjusting the pH to pH 2. An orange solid was isolated by filtration. This solid was slurried in water (30 ml) followed by ethyl acetate (30 ml) and dichloromethane (30 ml), and isolated by filtration as a yellow solid (2.0 g, 45%).

Workup

  1. customto give a clear reaction mixture which
  2. stirringwas stirred at RT over the weekend
  3. customquenched with 2M HCl (200 ml)
  4. customAn orange solid was isolated by filtration

Sources & evidence

ORD record
ord-169ad7e3e7fa4c7ca57b982259a2dbc0
Source dataset
uspto-grants-2010_06
Patent number
US07728035B2

Reaction notes

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