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

HRID 2416169Notes

Reaction equation

HRID 2416169 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].CC(C)([O-])C.[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.COCCOCCOCCOCCO>[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

6

Reactant 2

HCID 117287Ethanone, 1-(2,6,6-trimethyl-3-cyclohexen-1-yl)-HCID 23665647Potassium tert-butoxide

Product 2

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

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 90263Tetraethylene glycol monomethyl etherSolvent

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 (100 g) synthesized in Referential Example 1, tetraethyleneglycol monomethyl ether (150 ml), potassium t-butoxide (25 g) and tetra-n-butylammonium bromide (2 g). Under stirring, they were reacted at 175° C. for 4 hours. The reaction mixture at this time was sampled and analyzed by gas chromatography, resulting in that the content of trans-2,6,6-trimethyl-3-cyclohexenyl methyl ketone (1a′) was 12%, while those of 2,6,6-trimethyl-2-cyclohexenyl methyl ketone (1b) and 2,6,6-trimethyl-1-cyclohexenyl methyl ketone (1c) produced by the above reaction were 61% and 27%, respectively.

Workup

  1. customIn a 500-ml four-necked flask equipped with a thermometer, a condenser and a stirrer
  2. customthey were reacted at 175° C. for 4 hours
  3. aliquotThe reaction mixture at this time was sampled

Sources & evidence

ORD record
ord-003a52ccc16e4300a266f82c260a3dab
Source dataset
uspto-grants-2004_11
Patent number
US06822121B2

Reaction notes

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