Diethyl Ether → HCID 67461255, compound

HRID 554065Notes

Reaction equation

HRID 554065 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]=[C:19]([C:21]([CH3:24])([CH3:23])[CH3:22])[CH:18]=[C:17]([CH2:25]Br)[CH:16]=1.[I-].[K+].[CH2:29]([O:31]CC)[CH3:30]>O>[C:21]([C:19]1[CH:18]=[C:17]([CH2:25][CH:3]([C:29](=[O:31])[CH3:30])[C:1](=[O:5])[CH3:4])[CH:16]=[C:15]([CH2:14][CH:9]([C:10](=[O:12])[CH3:11])[C:6](=[O:8])[CH3:7])[CH:20]=1)([CH3:24])([CH3:23])[CH3:22]

Participants

7

Reactant 5

HCID 3283Diethyl EtherHCID 4875Potassium IodideHCID 6386tert-ButanolHCID 31261AcetylacetoneHCID 127079351,3-Bis(bromomethyl)-5-tert-butylbenzene

Product 1

HCID 67461255HCID 67461255, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
82 °C

Procedure

In a four-neck flask having a capacity of 500 mL, 19.6 g (175 mmol) of t-butokypotassium and 300 mL of t-butylalcohol were put in, agitated at a temperature of 82° C. for 30 minutes, dropped with 26.5 g (262 mmol) of acetylacetone at the temperature for 12 minutes, and then agitated for 2 hours. Thereafter, at 81 to 83° C., 25.0 g (87.3 mmol) of 1,3-bis(bromomethyl)-5-t-butylbenzene was added for 30 minutes, and then agitated for 1 hour. Thereafter, 3.49 g (21.0 mmol) of potassium iodide was added at 82° C., and then agitated for 3.5 hours. After the solution was cooled down to a room temperature, it was added with 100 mL of diethylether, and 115 mL of water to be subjected to an extraction operation, and then an organic layer was separated from a water layer. The organic layer obtained was added with 30 mL of saturated aqueous salt solution and agitated, and then an organic layer was separated from a water layer, dried with anhydrous sodium sulfate, and then concentrated by distilling off the solvent to obtain a crude product. The crude product obtained was purified with a silica gel column chromatography to obtain 21.9 g (yield 69%) of 3,3′-[5-t-butyl-1,3-phenylenebis(methylene)]bis(2,4-pentanedione)

Workup

  1. customIn a four-neck flask having
  2. stirringagitated for 2 hours
  3. stirringagitated for 1 hour
  4. stirringagitated for 3.5 hours
  5. temperatureAfter the solution was cooled down to a room temperature
  6. customan organic layer was separated from a water layer
  7. customThe organic layer obtained
  8. stirringagitated
  9. customan organic layer was separated from a water layer
  10. dry with materialdried with anhydrous sodium sulfate
  11. concentrationconcentrated
  12. distillationby distilling off the solvent
  13. customto obtain a crude product
  14. customThe crude product obtained
  15. customwas purified with a silica gel column chromatography

Sources & evidence

ORD record
ord-db698ac936db4bb69023a3d2fec2e1d6
Source dataset
uspto-grants-2011_11
Patent number
US08048982B2

Reaction notes

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