Butyl bromide → 3-Butylpentane-2,4-dione

HRID 732322Notes

Reaction equation

HRID 732322 reaction equation
[CH3:1][C:2](=[O:7])[CH2:3][C:4](=[O:6])[CH3:5].[CH2:8](Br)[CH2:9][CH2:10][CH3:11].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:8]([CH:3]([C:2](=[O:7])[CH3:1])[C:4](=[O:6])[CH3:5])[CH2:9][CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 8002Butyl bromideHCID 11430Potassium CarbonateHCID 31261Acetylacetone

Product 1

HCID 737633-Butylpentane-2,4-dioneYield 55.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2,4-pentanedione (205.4 ml, 2.0 mol), acetone (100 ml), n-butyl bromide (54 ml, 0.5 mol) and potassium carbonate (34.55 g, 0.25 mol) were put in a reaction vessel, purged with nitrogen and refluxed for 48 hours. The generated solid was filtered, and the solvent was removed using an evaporator. Unreacted-2,4-pentanedione was then removed under reduced pressure using a diaphragm. Then, vacuum distillation was then used to obtain 3-n-butyl-2,4-pentanedione (43.25 g, yield 55%).

Workup

  1. custompurged with nitrogen
  2. temperaturerefluxed for 48 hours
  3. filtrationThe generated solid was filtered
  4. customthe solvent was removed
  5. customan evaporator
  6. customUnreacted-2,4-pentanedione was then removed under reduced pressure
  7. distillationThen, vacuum distillation

Sources & evidence

ORD record
ord-b24e6cded68a40a1ac3aa3b604412ba0
Source dataset
uspto-grants-2009_09
Patent number
US07586117B2

Reaction notes

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