Diethyl Ether → 3,3'-[1,3-Phenylenebis(methylene)]di(pentane-2,4-dione)

HRID 554064Notes

Reaction equation

HRID 554064 reaction equation
[C:1]([OH:5])([CH3:4])([CH3:3])C.[C:6]([CH2:9][C:10](=[O:12])[CH3:11])(=[O:8])[CH3:7].Br[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21]Br)[CH:16]=1.[I-].[K+].[CH2:25]([O:27]CC)[CH3:26]>O>[C:17]1([CH2:21][CH:3]([C:25](=[O:27])[CH3:26])[C:1](=[O:5])[CH3:4])[CH:18]=[CH:19][CH:20]=[C:15]([CH2:14][CH:9]([C:10](=[O:12])[CH3:11])[C:6](=[O:8])[CH3:7])[CH:16]=1

Participants

7

Reactant 5

HCID 3283Diethyl EtherHCID 4875Potassium IodideHCID 6386tert-ButanolHCID 31261AcetylacetoneHCID 69373Benzene, 1,3-bis(bromomethyl)-

Product 1

HCID 666612163,3'-[1,3-Phenylenebis(methylene)]di(pentane-2,4-dione)

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

17.0 g (0.15 mol) of t-butokypotassium was added to 20 mL of t-butylalcohol, and then dissolved by agitating for 30 minutes under refluxing. In the above solution, under refluxing, 22.9 g (0.23 mol) of acetylacetone was dropped for 10 minutes, and then agitated for 2 hours. Thereafter, under refluxing, 20.2 g (0.08 mol) of 1,3-bis(bromomethyl)benzene was added for 30 minutes, and then agitated for 1 hour. Thereafter, under refluxing, 3.0 g (0.02 mol) of potassium iodide was added, and then agitated for 4 hours. After the completion of the agitation, the solution was cooled down to a room temperature, added with 100 mL of water, and 100 mL of diethylether, strongly agitated, and then an organic layer was separated from a water layer. The organic layer was washed twice with 100 mL of saturated aqueous salt solution, and then the organic layer was dried with anhydrous sodium sulfate, concentrated by removing the solvent and excess amount of acetylacetone under a reduced pressure to obtain a light-yellow oily crude product. The crude product was purified with a silica gel column chromatography to obtain a white solid (yield in amount 3.5 g, yield in ratio 15.1%)

Workup

  1. dissolutiondissolved
  2. temperatureunder refluxing
  3. temperatureIn the above solution, under refluxing
  4. stirringagitated for 2 hours
  5. temperatureThereafter, under refluxing
  6. stirringagitated for 1 hour
  7. temperatureThereafter, under refluxing
  8. stirringagitated for 4 hours
  9. stirringstrongly agitated
  10. customan organic layer was separated from a water layer
  11. washThe organic layer was washed twice with 100 mL of saturated aqueous salt solution
  12. dry with materialthe organic layer was dried with anhydrous sodium sulfate
  13. concentrationconcentrated
  14. customby removing the solvent and excess amount of acetylacetone under a reduced pressure

Sources & evidence

ORD record
ord-c8d1743ff64a4674aee010fa38da9672
Source dataset
uspto-grants-2011_11
Patent number
US08048982B2

Reaction notes

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