2-Butyl-1,1,3-trimethylcyclohexane → 3-Butyl-2,4,4-trimethylcyclohex-2-en-1-one
Reaction equation
[Cr]([O-])(OC(C)(C)C)(=O)=[O:2].[CH3:10][CH:11]1[CH2:16][CH2:15][CH2:14][C:13]([CH3:18])([CH3:17])[CH:12]1[CH2:19][CH2:20][CH2:21][CH3:22]>>[CH3:10][C:11]1[C:16](=[O:2])[CH2:15][CH2:14][C:13]([CH3:17])([CH3:18])[C:12]=1[CH2:19][CH2:20][CH2:21][CH3:22]Participants
3
Procedure
18 g Of the mixture of alkenes obtained by dehydration of dihydro-β-ionol as described in example 1 was dissolved in 150 ml of methanol and hydrogenated at atmospheric pressure using 0.5 g of a catalyst consisting of 5% Palladium on charcoal. Hydrogenation was stopped when the uptake of hydrogen markedly slowed down. A 1:1 mixture of 1,3,3-trimethyl-2-(but-1-yl)-cyclohex-1-ene and 1,3,3-trimethyl-2-(but-1-yl)-cyclohexane was obtained. This mixture was oxidized with tert.butyl chromate as described in example 1, yielding a mixture of the title compound and 1,3,3-trimethyl-2-(but-1-yl)-cyclohexane. The mixture was fractionated yielding 6.75 g of the title compound boiling at 90°-92° C. (4 Torr).
Workup
- customyielding
Sources & evidence
- ORD record
- ord-affb8a9339e54116bf97b92069c250a8
- Source dataset
- uspto-grants-1981_01
- Patent number
- US04246292
Reaction notes
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