p-Toluenesulfonic acid → N,N-dimethyl-2-(4-oxocyclohexyl)acetamide

HRID 243565Notes

Reaction equation

HRID 243565 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:12][N:13]([CH3:27])[C:14](=[O:26])[CH2:15][CH:16]1[CH2:25][CH2:24][C:19]2(OCC[O:20]2)[CH2:18][CH2:17]1>CC(C)=O>[CH3:27][N:13]([CH3:12])[C:14](=[O:26])[CH2:15][CH:16]1[CH2:25][CH2:24][C:19](=[O:20])[CH2:18][CH2:17]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 59442805N,N-dimethyl-2-(1,4-dioxaspiro[4.5]decan-8-yl)acetamide

Product 1

HCID 59442836N,N-dimethyl-2-(4-oxocyclohexyl)acetamideYield 99.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

p-Toluenesulfonic acid (84 mg) is added to a solution of N,N-dimethyl-2-(1,4-dioxaspiro[4.5]decan-8-yl)acetamide (500 mg) in acetone (10 ml) and the mixture is heated under reflux for 3 hours. The solvent is removed under reduced pressure. The residue is dissolved in CH2Cl2 and washed with water. The organic layer is dried (Na2SO4) and filtered, and the solvent is removed under reduced pressure to give N,N-dimethyl-2-(4-oxocyclohexyl)acetamide (400 mg).

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 3 hours
  3. customThe solvent is removed under reduced pressure
  4. dissolutionThe residue is dissolved in CH2Cl2
  5. washwashed with water
  6. dry with materialThe organic layer is dried (Na2SO4)
  7. filtrationfiltered
  8. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-51a304ae37d4451fb65828b5bd44e609
Source dataset
uspto-grants-2014_02
Patent number
US08653262B2

Reaction notes

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