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

HRID 1441793Notes

Reaction equation

HRID 1441793 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-fa2c232237404c3091eb4f726819c5a9
Source dataset
uspto-grants-2010_02
Patent number
US07655689B2

Reaction notes

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