2-Cyclohexenone, 5,5-dimethyl- → Cyclohexanone, 3,3-dimethyl-

HRID 25885Notes

Reaction equation

HRID 25885 reaction equation
[CH3:1][C:2]1([CH3:9])[CH2:7][CH:6]=[CH:5][C:4](=[O:8])[CH2:3]1>[Pd]>[CH3:1][C:2]1([CH3:9])[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[CH2:3]1

Participants

3

Reactant 1

HCID 1383222-Cyclohexenone, 5,5-dimethyl-

Product 1

HCID 76322Cyclohexanone, 3,3-dimethyl-

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

(a') A catalytic hydrogenation of 3,3-dimethyl-cyclohex-5-en-1-one was carried out according to the usual techniques in the presence of palladium on charcoal and yielded 3,3-dimethylcyclohexanone. The subsequent ethylination by means of acetylene in a basic medium gave 1-ethynyl-1-hydroxy-3,3-dimethyl-cyclohexane in about 50% yield.

Sources & evidence

ORD record
ord-7fd5cdd43d444ba7b113a4b8707587e0
Source dataset
uspto-grants-1979_04
Patent number
US04147672

Reaction notes

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