Anthrone → Ethanol, 2-(9-anthracenyloxy)-

HRID 590642Notes

Reaction equation

HRID 590642 reaction equation
[CH:1]1[C:14]2[C:13](=[O:15])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:23][CH2:24][OH:25]>CN(C=O)C>[CH:11]1[C:12]2[C:7](=[CH:6][C:5]3[C:14]([C:13]=2[O:15][CH2:23][CH2:24][OH:25])=[CH:1][CH:2]=[CH:3][CH:4]=3)[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 7018AnthroneHCID 108982-BromoethanolHCID 11430Potassium Carbonate

Product 1

HCID 11265428Ethanol, 2-(9-anthracenyloxy)-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of anthrone (5.0 g, 25.7 mmole) in 34 mL anhydrous DMF under an inert atmosphere was added potassium carbonate (7.47 g, 54.1 mmole). To the resulting reaction mixture was added 2-bromoethanol (2.0 mL, 28.3 mmole). The resulting reaction mixture was stirred for 1 hr at room temperature, then 3 hrs at 80° C. The reaction was then cooled to room temperature and quenched with saturated NaHCO3. Ethyl acetate was added and the organic layer was collected and dried over magnesium sulfate. The solvent was concentrated under reduced pressure and the residue was purified via flash chromatography.

Workup

  1. customTo the resulting reaction mixture
  2. customThe resulting reaction mixture
  3. custom3 hrs
  4. customat 80° C
  5. temperatureThe reaction was then cooled to room temperature
  6. customquenched with saturated NaHCO3
  7. additionEthyl acetate was added
  8. customthe organic layer was collected
  9. dry with materialdried over magnesium sulfate
  10. concentrationThe solvent was concentrated under reduced pressure
  11. customthe residue was purified via flash chromatography

Sources & evidence

ORD record
ord-5d7b9a263d86414abb91f2db5d548325
Source dataset
uspto-grants-2016_01
Patent number
US09234153B2

Reaction notes

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