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

HRID 2416172Notes

Reaction equation

HRID 2416172 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].C[O-].[K+].C1CCCCCCCCCCC1.[CH3:28][C:29]([C@@H:31]1[C:36]([CH3:38])([CH3:37])[CH2:35][CH:34]=[CH:33][C@H:32]1[CH3:39])=[O:30]>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].[CH3:28][C:29]([C:31]1[C:36]([CH3:38])([CH3:37])[CH2:35][CH2:34][CH2:33][C:32]=1[CH3:39])=[O:30]

Participants

7

Reactant 4

HCID 9268CyclododecaneHCID 117287Ethanone, 1-(2,6,6-trimethyl-3-cyclohexen-1-yl)-HCID 23664618Potassium methoxideHCID 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 methoxide (2.5 g), dimethyl sulfoxide (30 ml) and, as an internal standard substance for the analysis by gas chromatography, cyclododecane (3 g). The mixture was reacted at 120° C. for 2.5 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 4.4%, 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 69.8% and 25.8%, respectively. As a result of calculation, the yield of the mixture of these three methyl ketones was found to be 8.6 g.

Workup

  1. customIn a 100-ml four-necked flask equipped with a thermometer, a condenser and a stirrer
  2. customThe mixture was reacted at 120° C. for 2.5 hours
  3. additionThe reaction mixture was treated in an usual manner

Sources & evidence

ORD record
ord-3ad9d001e69d4064be89745d6b0cf079
Source dataset
uspto-grants-2004_11
Patent number
US06822121B2

Reaction notes

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