Acetone → 2,2,6,6-Tetramethyl-4-piperidone

HRID 1077000Notes

Reaction equation

HRID 1077000 reaction equation
[CH3:1][C:2]1[CH2:7][C:6]([CH3:9])([CH3:8])[NH:5][C:4]([CH3:11])([CH3:10])N=1.CC(C)=[O:14].CO.ClC(Cl)C(O)=O>O>[CH3:10][C:4]1([CH3:11])[NH:5][C:6]([CH3:9])([CH3:8])[CH2:7][C:2](=[O:14])[CH2:1]1

Participants

6

Reactant 4

HCID 180AcetoneHCID 887MethanolHCID 6597Dichloroacetic AcidHCID 68396Pyrimidine, 1,2,5,6-tetrahydro-2,2,4,6,6-pentamethyl-

Product 1

HCID 132202,2,6,6-Tetramethyl-4-piperidoneYield 136%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

15.4 g. of Acetonine was dissolved in a mixed solvent comprising 169.8 g. of acetone and 56.6 g. of methanol. The solution was ice-cooled, added with 12.9 g. of dichloroacetic acid and 1.8 g. of water under stirring. The mixture was stirred at room temperature for 24 hours to effect the reaction. After completion of the reaction, the reaction mixture was concentrated under reduced pressure, added with 40% aqueous potassium carbonate solution and extracted with ether. The extract was dried over anhydrous potassium carbonate, then ether was distilled off and the resulting residue was purified by distillation under reduced pressure to obtain triacetonamine in a yield of 136%.

Workup

  1. temperaturecooled
  2. additionadded with 12.9 g
  3. customthe reaction
  4. customAfter completion of the reaction
  5. concentrationthe reaction mixture was concentrated under reduced pressure
  6. additionadded with 40% aqueous potassium carbonate solution
  7. extractionextracted with ether
  8. dry with materialThe extract was dried over anhydrous potassium carbonate
  9. distillationether was distilled off
  10. distillationthe resulting residue was purified by distillation under reduced pressure

Sources & evidence

ORD record
ord-b66e1610d87143bf9b7690e6c289ff02
Source dataset
uspto-grants-1976_05
Patent number
US03959298

Reaction notes

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