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

HRID 2416173Notes

Reaction equation

HRID 2416173 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-].[Na+].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 10942334Sodium 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, sodium methoxide (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 140 to 145° C. for 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 28.9%, 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 49.2% and 21.9%, respectively. As a result of calculation, the yield of a mixture of these three methyl ketones was found to be 7.3 g.

Workup

  1. customIn a 100-ml four-necked flask equipped with a thermometer, a condenser and a stirrer
  2. customThey were reacted at 140 to 145° C. for 5 hours
  3. additionThe reaction mixture was treated in an usual manner

Sources & evidence

ORD record
ord-260f33a899b444269e686829740f4fa3
Source dataset
uspto-grants-2004_11
Patent number
US06822121B2

Reaction notes

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