Allyl bromide → 2,4-Pentanedione, 3-(2-propenyl)-

HRID 1907069Notes

Reaction equation

HRID 1907069 reaction equation
[OH-].[Na+].[C:3]([CH2:6][C:7](=[O:9])[CH3:8])(=[O:5])[CH3:4].[CH2:10](Br)[CH:11]=[CH2:12]>CO>[CH2:12]([CH:6]([C:7](=[O:9])[CH3:8])[C:3](=[O:5])[CH3:4])[CH:11]=[CH2:10]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 14798Sodium HydroxideHCID 31261Acetylacetone

Product 1

HCID 190232,4-Pentanedione, 3-(2-propenyl)-Yield 48%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

NaOH (4.51 g, 113 mmol) was dissolved in anhydrous MeOH. After cooling the mixture to 0° C. using an ice-bath, acetylacetone (10.0 g, 99.8 mmol) was added while stirring over a period of several minutes. Allyl bromide (10.4 mL, 123 mmol) was then added without cooling over a period of 10 min. After addition was complete, the reaction mixture was refluxed for an additional 2 h. The mixture was cooled and filtered to remove excess NaBr. MeOH and the excess allyl bromide were removed by distillation. The product, 5, was isolated as a yellow oil, 6.72 g (48% yield), between 81-87° C.

Workup

  1. temperaturewithout cooling over a period of 10 min
  2. additionAfter addition
  3. temperaturethe reaction mixture was refluxed for an additional 2 h
  4. temperatureThe mixture was cooled
  5. filtrationfiltered
  6. customto remove excess NaBr
  7. customMeOH and the excess allyl bromide were removed by distillation
  8. customThe product, 5, was isolated as a yellow oil, 6.72 g (48% yield), between 81-87° C.

Sources & evidence

ORD record
ord-7acba4c4ad19485daa32e96c3811725f
Source dataset
uspto-grants-2013_12
Patent number
US08597803B2

Reaction notes

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