2-Ethylanthraquinone → HCID 22315883, compound

HRID 394412Notes

Reaction equation

HRID 394412 reaction equation
[CH2:1]([C:3]1[CH:16]=[CH:15][C:14]2[C:13](=[O:17])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6](=[O:18])[C:5]=2[CH:4]=1)[CH3:2].C1C(=O)N([Br:26])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:26][CH:1]([C:3]1[CH:16]=[CH:15][C:14]2[C:13](=[O:17])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6](=[O:18])[C:5]=2[CH:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 67722-EthylanthraquinoneHCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimide

Product 1

HCID 22315883HCID 22315883, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 2-ethylanthraquinone (25 Kg, 105.9 mol), NBS (19.1 Kg, 107.3 mol) and benzoyl peroxide (70%, 200 g, 0.58 mol) in CCl4 (˜150L) is stirred at reflux for 1.5 hours. On cooling, the precipitate is collected by filtration and washed on the filter with ethanol, hot water and finally ethanol again. After drying, this may be used without further purification (i.e. recrystallisation from benzene/methanol (1:1)).

Workup

  1. temperatureat reflux for 1.5 hours
  2. temperatureOn cooling
  3. filtrationthe precipitate is collected by filtration
  4. washwashed on the
  5. filtrationfilter with ethanol, hot water and finally ethanol again
  6. customAfter drying
  7. customthis may be used without further purification (i.e. recrystallisation from benzene/methanol (1:1))

Sources & evidence

ORD record
ord-237bc96903554e8db12240565a2768d7
Source dataset
uspto-grants-2003_08
Patent number
US06601732B1

Reaction notes

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