Acetone → 2,2-Dimethyl-2,4-dihydro-1,3-dioxin-4-one

HRID 65120Notes

Reaction equation

HRID 65120 reaction equation
CC(C)=O.[CH3:5][C:6]1([CH3:16])[O:15][C:13](=O)[C:10](=CO)[C:8](=[O:9])[O:7]1>C1(C)C=CC=CC=1>[CH3:5][C:6]1([CH3:16])[O:7][C:8](=[O:9])[CH:10]=[CH:13][O:15]1

Participants

4

Reactant 2

HCID 180AcetoneHCID 111375775-(Hydroxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 131570352,2-Dimethyl-2,4-dihydro-1,3-dioxin-4-oneYield 82.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Acetone (2.9 g) was added to sufficiently dehydrated toluene (500 ml) and the mixture was heated under reflux in a reaction flask equipped with a reflux condenser. While the reflux was continued, a warm solution obtained by dissolving formyl Meldrum's acid (8.6 g) in toluene (500 ml) on heating was dropwise added over about 2 hours, followed by subjecting the reaction mixture to heating under reflux for additional one hour and then subjecting the resulting reaction mixture to purifying operation in the same manner as in Example 1 to obtain 2,2-dimethyl-1,3-dioxin-4-one (5.3 g, yield 82%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux in a reaction flask
  3. customequipped with a reflux condenser
  4. customa warm solution obtained
  5. temperatureon heating
  6. additionwas dropwise added over about 2 hours
  7. temperatureto heating
  8. temperatureunder reflux for additional one hour
  9. customthe resulting reaction mixture
  10. customto purifying operation in the same manner as in Example 1

Sources & evidence

ORD record
ord-0089afd24a384655ad86819e2ed2a612
Source dataset
uspto-grants-1986_09
Patent number
US04612379

Reaction notes

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