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

HRID 2078022Notes

Reaction equation

HRID 2078022 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 fed into a reaction vessel, air in the vessel was replaced with nitrogen, and reflux was carried out for 48 hours. The resultant solid was filtered out, and the solvent was distilled off by means of an evaporator. After that, unreacted 2,4-pentanedione was distilled off under reduced pressure by means of a diaphragm. Then, the remainder was distilled in a vacuum to yield 3-n-butyl 2,4-pentanedione (43.25 g, 55% yield).

Workup

  1. temperaturereflux
  2. filtrationThe resultant solid was filtered out
  3. distillationthe solvent was distilled off by means of an evaporator
  4. distillationAfter that, unreacted 2,4-pentanedione was distilled off under reduced pressure by means of a diaphragm
  5. distillationThen, the remainder was distilled in a vacuum

Sources & evidence

ORD record
ord-51bb00867c1e4642bb1cfb8d12896db8
Source dataset
uspto-grants-2011_04
Patent number
US07928221B2

Reaction notes

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