Реакция #1771995

Уравнение реакции

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

→

4,4-dimethylcyclohexanone

Выход 64.3%

Условия реакции

Обработка

1. 1
   ФильтрацияThe mixture was filtered
2. 2
   Концентрированиеconcentrated (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
   Другоеthe cooling bath was removed
7. 7
   ДругоеAfter 2 days the excess acetone was evaporated
8. 8
   workup.DISSOLUTIONthe resulting residue was dissolved in water
9. 9
   ПромывкаThe ether layer was washed with water until colorless,
10. 10
    Другоеdried
11. 11
    Фильтрацияfiltered
12. 12
    Концентрированиеconcentrated

Методика

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%).

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