반응 #1771995

반응 방정식

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

→

4,4-dimethylcyclohexanone

수율 64.3%

반응 조건

후처리

1. 1
   여과The mixture was filtered
2. 2
   농축concentrated (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
   기타the cooling bath was removed
7. 7
   기타After 2 days the excess acetone was evaporated
8. 8
   workup.DISSOLUTIONthe resulting residue was dissolved in water
9. 9
   세척The ether layer was washed with water until colorless,
10. 10
    기타dried
11. 11
    여과filtered
12. 12
    농축concentrated

실험 절차

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%).

출처