p-Toluenesulfonic acid → Ethanone, 1-(2,6,6-trimethyl-3-cyclohexen-1-yl)-

HRID 2416171Notes

Reaction equation

HRID 2416171 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].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:1][C:2]([C@@H:4]1[C:9]([CH3:11])([CH3:10])[CH2:8][CH:7]=[CH:6][C@H:5]1[CH3:12])=[O:3].[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]

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 117287Ethanone, 1-(2,6,6-trimethyl-3-cyclohexen-1-yl)-

Product 2

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a 500-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, toluene (100 ml) and p-toluenesulfonic acid (2 g). Under stirring, they were reacted at 125° C. for 6 hours. The reaction mixture sampled at this time was analyzed by gas chromatography, resulting in that the content of trans-2,6,6-trimethyl-3-cyclohexenyl methyl ketone (1a′) was 17%, that of 2,6,6-trimethyl-2-cyclohexenyl methyl ketone (1b) was 56.5%, and that of 2,6,6-trimethyl-1-cyclohexenyl methyl ketone (1c) was 26.5%.

Workup

  1. customIn a 500-ml four-necked flask equipped with a thermometer, a condenser and a stirrer
  2. customthey were reacted at 125° C. for 6 hours
  3. aliquotThe reaction mixture sampled at this time

Sources & evidence

ORD record
ord-ee839252bba04f789a625146edff45d7
Source dataset
uspto-grants-2004_11
Patent number
US06822121B2

Reaction notes

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