Reaction #1771995

Reaction equation

4,4-dimethylcyclohex-2-en-1-one

→

4,4-dimethylcyclohexanone

Yield 64.3%

Conditions

Workup

1. 1
   FiltrationThe mixture was filtered
2. 2
   Concentrationconcentrated (1H NMR
3. 3
   workup.ADDITIONa mixture of ketone and alcohol in a 5:3 ratio)
4. 4
   workup.DISSOLUTIONThe mixture was dissolved in acetone (400 mL)
5. 5
   workup.ADDITIONJones reagent (40 mL) was added over 30 min
6. 6
   Otherthe cooling bath was removed
7. 7
   OtherAfter 2 days the excess acetone was evaporated
8. 8
   workup.DISSOLUTIONthe resulting residue was dissolved in water
9. 9
   WashThe ether layer was washed with water until colorless,
10. 10
    Otherdried
11. 11
    Filtrationfiltered
12. 12
    Concentrationconcentrated

Procedure

A mixture of 4,4-dimethylcyclohex-2-en-1-one (12 mL, 91.2 mmol) and Degussa type 10% Pd on carbon (2 g) was hydrogenated at 40 psi for 18 hours. The mixture was filtered and concentrated (1H NMR showed a mixture of ketone and alcohol in a 5:3 ratio). The mixture was dissolved in acetone (400 mL) and cooled to 0° C. Jones reagent (40 mL) was added over 30 min and the cooling bath was removed. After 2 days the excess acetone was evaporated and the resulting residue was dissolved in water and diethylether. The ether layer was washed with water until colorless, dried, filtered and concentrated to give 4,4-dimethylcyclohexanone (7.4 g, 58.6 mmol, 64%).

Source