Acetone → 1,3-Dioxane-4,6-dione, 2,2-dimethyl-5-(2-propenyl)-

HRID 552035Notes

Reaction equation

HRID 552035 reaction equation
[CH3:1][C:2]1([CH3:11])[O:7][C:6](=[O:8])[CH:5]([CH3:9])[C:4](=[O:10])[O:3]1.[CH2:12](Br)[CH:13]=C.C(=O)([O-])[O-].[K+].[K+].CC(C)=O>C(OCC)C>[CH3:11][C:2]1([CH3:1])[O:3][C:4](=[O:10])[CH:5]([CH2:9][CH:12]=[CH2:13])[C:6](=[O:8])[O:7]1

Participants

6

Reactant 4

HCID 180AcetoneHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 772992,2,5-Trimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 112291701,3-Dioxane-4,6-dione, 2,2-dimethyl-5-(2-propenyl)-Yield 94.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a 500 mL 3-necked round bottomed flask equipped with a stir bar, thermowell and a condenser connected to a nitrogen line was added 10.0 g (0.0632 mole) of 2,2,5-trimethyl-1,3-dioxane-4,6-dione, 7.7 g (0.0632 mol) of allyl bromide, 21 g (0.152 mol) of potassium carbonate and 200 mL of acetone. The mixture was refluxed with stirring overnight at which time it was allowed to cool, diluted with 200 mL of ethyl ether and filtered through a bed of Celite/activated charcoal. The filtrate was washed with water and brine and dried overnight over anhydrous sodium sulfate. The suspension was filtered and the filtrate evaporated on a rotary evaporator to yield 11 g of 2,2-dimethyl-5-allyl-1,3-dioxane-4,6-dione compound as shown in Formula (IV)) as a clear, colorless oil.

Workup

  1. customTo a 500 mL 3-necked round bottomed flask equipped with a stir bar
  2. customthermowell and a condenser connected to a nitrogen line
  3. temperatureThe mixture was refluxed
  4. temperatureto cool
  5. filtrationfiltered through a bed of Celite/activated charcoal
  6. washThe filtrate was washed with water and brine
  7. dry with materialdried overnight over anhydrous sodium sulfate
  8. filtrationThe suspension was filtered
  9. customthe filtrate evaporated on a rotary evaporator

Sources & evidence

ORD record
ord-d0504deea8c14d0a9b0584d9eae53de1
Source dataset
uspto-grants-2011_05
Patent number
US07951525B2

Reaction notes

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