反応 #1771995

反応方程式

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

→

4,4-dimethylcyclohexanone

収率 64.3%

反応条件

後処理

1. 1
   ろ過The mixture was filtered
2. 2
   濃縮concentrated (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
   その他the cooling bath was removed
7. 7
   その他After 2 days the excess acetone was evaporated
8. 8
   workup.DISSOLUTIONthe resulting residue was dissolved in water
9. 9
   洗浄The ether layer was washed with water until colorless,
10. 10
    その他dried
11. 11
    ろ過filtered
12. 12
    濃縮concentrated

実験手順

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%).

出典