2,6-Dihydroxyanthraquinone → 2,6-Bis((2-ethylhexyl)oxy)anthracene-9,10-dione

HRID 900387

Reaction equation

HRID 900387 reaction equation
[OH:1][C:2]1[CH:15]=[CH:14][C:13]2[C:12](=[O:16])[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([OH:17])[CH:10]=3)[C:5](=[O:18])[C:4]=2[CH:3]=1.[CH2:19]([CH:21]([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:22]Br)[CH3:20].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:19]([CH:21]([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:22][O:1][C:2]1[CH:15]=[CH:14][C:13]2[C:12](=[O:16])[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([O:17][CH2:5][CH:4]([CH2:13][CH3:12])[CH2:3][CH2:2][CH2:15][CH3:14])[CH:10]=3)[C:5](=[O:18])[C:4]=2[CH:3]=1)[CH3:20]

Participants

5

Reactant 3

HCID 67762,6-DihydroxyanthraquinoneHCID 11430Potassium CarbonateHCID 868042-Ethylhexyl bromide

Product 1

HCID 224722982,6-Bis((2-ethylhexyl)oxy)anthracene-9,10-dioneYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Into a 500 ml flask, 10 g (42 mmole) of 2,6-dihydroxyanthraquinone, 16.5 g (86 mmole) of 2-ethylhexyl bromide, 12 g (87 mmole) of anhydrous potassium carbonate and 200 ml of dimethylformamide (DMF) were placed, and the resultant mixture was heated at 90° C. under stirring for one night. After the reaction was completed, DMF was removed by distillation, and 50 ml of water was added. The reaction solution was treated by extraction with diethyl ether, washed with a saturated aqueous solution of sodium chloride and dried with magnesium sulfate. After the concentration under a reduced pressure, the obtained crude product was recrystallized from methanol, and 12.5 g of the quinone compound of the object compound was obtained (the yield: 65%; a yellow powder).

Workup

  1. customDMF was removed by distillation, and 50 ml of water
  2. additionwas added
  3. additionThe reaction solution was treated by extraction with diethyl ether
  4. washwashed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried with magnesium sulfate
  6. concentrationAfter the concentration under a reduced pressure
  7. customthe obtained crude product
  8. customwas recrystallized from methanol, and 12.5 g of the quinone compound of the object compound
  9. customwas obtained (the yield: 65%

Sources & evidence

ORD record
ord-d4ee0a9ab4c046858a950859cbe14980
Source dataset
uspto-grants-2008_04
Patent number
US07357991B2

Linked notes

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