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

HRID 1297557Notes

Reaction equation

HRID 1297557 reaction equation
[CH3:1][C@@H:2]1[CH:7]=[CH:6][CH2:5][C:4]([CH3:9])([CH3:8])[C@H:3]1[C:10](=[O:12])[CH3:11].B(F)(F)F>>[CH3:1][CH:2]1[CH:7]=[CH:6][CH2:5][C:4]([CH3:8])([CH3:9])[CH:3]1[C:10](=[O:12])[CH3:11]

Participants

3

Reactant 2

HCID 6356Boron trifluorideHCID 54437493Trans-4-Acetyl-3,5,5-Trimethylcyclohexene

Product 1

HCID 117287Ethanone, 1-(2,6,6-trimethyl-3-cyclohexen-1-yl)-

Conditions

Temperature
130 °C

Procedure

To trans 1-(2,6,6-trimethyl-3-cyclohexen-1-yl)-1-ethanone (4.52 mol; trans/cis=94/5 to 99/1, purity≧99%) stirred under nitrogen at 20° C. was added BF3.(AcOH)2 (2.27 mmol of BF3) and [Ru(COD)(methallyl)2] (2.27 mmol) was added consecutively. The resulting solution was heated to 130° C. and stirred over 30 minutes at 130° C. under nitrogen. Afterwards, the resulting mixture was cooled to 20° C. and there was obtained a mixture comprising (% by weight of the final mixture, obtained by GC analysis):

Workup

  1. temperatureAfterwards, the resulting mixture was cooled to 20° C.
  2. customthere was obtained a mixture
  3. customobtained by GC analysis):

Sources & evidence

ORD record
ord-ff2e1fc0444340beb1681e00b0db2fc3
Source dataset
uspto-grants-2007_07
Patent number
US07250536B2

Reaction notes

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