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

HRID 1297556Notes

Reaction equation

HRID 1297556 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].[H+].[B-](F)(F)(F)F.O(CC)CC>>[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

4

Reactant 3

HCID 3283Diethyl EtherHCID 28118Tetrafluoroboric acidHCID 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 HBF4.OEt2 (4.54 mmol of HBF4) and [Ru(COD)(methallyl)2] (4.54 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-7f51d90b273f4446879af1e1b8a9b152
Source dataset
uspto-grants-2007_07
Patent number
US07250536B2

Reaction notes

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