2-Cyclohexen-1-one, 4,4-dimethyl- → Cyclohexanone, 4,4-dimethyl-

Temperature

0 °C

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%). Step 2. Synthesis of the Methyl Enol Ether of 4,4-Dimethylcyclohexylcarboxaldehyde:

1. filtrationThe mixture was filtered
2. concentrationconcentrated (1H NMR
3. additiona mixture of ketone and alcohol in a 5:3 ratio)
4. dissolutionThe mixture was dissolved in acetone (400 mL)
5. additionJones reagent (40 mL) was added over 30 min
6. customthe cooling bath was removed
7. customAfter 2 days the excess acetone was evaporated
8. dissolutionthe resulting residue was dissolved in water
9. washThe ether layer was washed with water until colorless,
10. customdried
11. filtrationfiltered
12. concentrationconcentrated

ORD record

ord-b1cf16a588cb42c4ad488f710d724437

Source dataset

uspto-grants-2006_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07012066B2