Dimethylformamide → 2-[(2-ethylhexyl)oxy]-7H-benzo[de]anthracene-7-one

HRID 1861215Notes

Reaction equation

HRID 1861215 reaction equation
[OH:1][C:2]1[CH:19]=[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]3[C:11](=[O:18])[C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=4[C:4](=[C:5]23)[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:26]([CH:28]([CH2:31][CH2:32][CH2:33][CH3:34])[CH2:29]Br)[CH3:27].CN(C)C=O>O>[CH2:26]([CH:28]([CH2:31][CH2:32][CH2:33][CH3:34])[CH2:29][O:1][C:2]1[CH:19]=[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]3[C:11](=[O:18])[C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=4[C:4](=[C:5]23)[CH:3]=1)[CH3:27]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 868042-Ethylhexyl bromide2×HCID 112420342-Hydroxybenzanthrone

Product 1

HCID 225971782-[(2-ethylhexyl)oxy]-7H-benzo[de]anthracene-7-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 500 ml three neck flask was equipped with a mechanical stirrer, heating mantle and condenser. To the flask was added 25 g 2-hydroxy-7H-benzo[de]anthracene-7-one, 18 g powdered potassium carbonate, 25 g 2-ethylhexyl bromide and 250 g dimethylformamide (DMF). The mixture was heated to reflux. After seven hours, 4.5 g 2-ethylhexyl bromide was added and the mixture heated at reflux for an additional three hours. The mixture was then cooled to room temperature and 500 g deionized water was added. The solution was extracted twice with 200 g chloroform. The organic layers were combined and washed twice with 250 g water. The solvent was removed on a rotary evaporator, then the crude product was passed through a flash silica gel column using methylene chloride as the elutant. The product fractions were collected and the solvent removed using a rotary evaporator. The yield of 2-[(2-ethylhexyl)oxy]-7H-benzo[de]anthracene-7-one was 28.5 g.

Workup

  1. temperatureheating mantle and condenser
  2. temperatureThe mixture was heated to reflux
  3. temperaturethe mixture heated
  4. temperatureat reflux for an additional three hours
  5. additionwas added
  6. extractionThe solution was extracted twice with 200 g chloroform
  7. washwashed twice with 250 g water
  8. customThe solvent was removed on a rotary evaporator
  9. customThe product fractions were collected
  10. customthe solvent removed
  11. customa rotary evaporator

Sources & evidence

ORD record
ord-0a289f8628db4f4eb0a5878d1f23ca43
Source dataset
uspto-grants-2003_03
Patent number
US06531613B1

Reaction notes

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