Cyclododecane → 1-(2,6,6-Trimethyl-1-cyclohexen-1-yl)ethanone

HRID 2416176Notes

Reaction equation

HRID 2416176 reaction equation
[CH3:1][C:2]([CH:4]1[C:9]([CH3:11])([CH3:10])[CH2:8][CH:7]=[CH:6][CH:5]1[CH3:12])=[O:3].[OH-].[K+].C1CCCCCCCCCCC1.[CH3:27][C:28]([C@@H:30]1[C:35]([CH3:37])([CH3:36])[CH2:34][CH:33]=[CH:32][C@H:31]1[CH3:38])=[O:29]>CS(C)=O>[CH3:1][C:2]([CH:4]1[C:9]([CH3:11])([CH3:10])[CH2:8][CH2:7][CH:6]=[C:5]1[CH3:12])=[O:3].[CH3:27][C:28]([C:30]1[C:35]([CH3:37])([CH3:36])[CH2:34][CH2:33][CH2:32][C:31]=1[CH3:38])=[O:29]

Participants

7

Reactant 4

HCID 9268CyclododecaneHCID 14797Potassium HydroxideHCID 117287Ethanone, 1-(2,6,6-trimethyl-3-cyclohexen-1-yl)-HCID 54437493Trans-4-Acetyl-3,5,5-Trimethylcyclohexene

Product 2

HCID 5393161-(2,6,6-Trimethyl-1-cyclohexen-1-yl)ethanoneHCID 157476822,6,6-Trimethyl-2-cyclohexenyl methyl ketone

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In a 100-ml four-necked flask equipped with a thermometer, a condenser and a stirrer, placed were 2,6,6-trimethyl-3-cyclohexenyl methyl ketone (10 g) synthesized in Referential Example 1, potassium hydroxide (2.5 g), dimethyl sulfoxide (30 ml) and, as an internal standard substance for the analysis by gas chromatography, cyclododecane (3 g). They were reacted at 170 to 190° C. for 6 hours. The reaction mixture was treated in an usual manner. Analysis by gas chromatography showed that the content of trans-2,6,6-trimethyl-3-cyclohexenyl methyl ketone was 67.5%, while those of 2,6,6-trimethyl-2-cyclohexenyl methyl ketone and 2,6,6-trimethyl-1-cyclohexenyl methyl ketone produced by the above reaction were 20.1% and 12.4%, respectively. As a result of calculation, the yield of a mixture of these three methyl ketones was found to be 4.3 g.

Workup

  1. customIn a 100-ml four-necked flask equipped with a thermometer, a condenser and a stirrer
  2. customThey were reacted at 170 to 190° C. for 6 hours
  3. additionThe reaction mixture was treated in an usual manner

Sources & evidence

ORD record
ord-949eda96cd314b4885a4d65ef6ad8964
Source dataset
uspto-grants-2004_11
Patent number
US06822121B2

Reaction notes

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