Acetone → 3,4-Dimethylhexane-2,5-dione

HRID 2110416Notes

Reaction equation

HRID 2110416 reaction equation
[CH3:1][C:2]1[O:3][C:4]([CH3:9])=[C:5]([CH3:8])[C:6]=1[CH3:7].CC(=[O:13])C>>[CH3:7][CH:6]([CH:5]([CH3:8])[C:4](=[O:3])[CH3:9])[C:2](=[O:13])[CH3:1]

Participants

3

Reactant 2

HCID 180AcetoneHCID 1391982,3,4,5-tetramethylfuran

Product 1

HCID 328513,4-Dimethylhexane-2,5-dioneYield 42.5%

Procedure

Compound 219A was made in accordance with the procedures described in Hancock et al. J. Org. Chem. 42,1850-1856 (1977) & Amarnath et al. J. Org. Chem., 60, 301-307 (1995). 2-Propanone (100 mL, 1.1 mol) was refluxed over PbO2 (26.7 g, 0.112 mol) for 28 h. After cooling to rt, the reaction mixture was filtered and the residue was washed with acetone. The filtrate was concentrated under reduced pressure to remove the acetone and then distilled at 20 Torr. The fraction that came over between 100-120° C. was collected to give 6.75 g (42.5%) of 3,4-dimethylhexane-2,5-dione as a light yellow oil.

Workup

  1. filtrationthe reaction mixture was filtered
  2. washthe residue was washed with acetone
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customto remove the acetone
  5. distillationdistilled at 20 Torr
  6. customcame over between 100-120° C.
  7. customwas collected

Sources & evidence

ORD record
ord-29f0c02771a246868ee7e43af6e97629
Source dataset
uspto-grants-2009_04
Patent number
US07517904B2

Reaction notes

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