Methanol → 2,6,9,11-Dodecatetraenal, 2,6,10-trimethyl-, (2E,6E,9E)-
Reaction equation
C[C:2]([CH:15]=C)([CH:5](C(C)=C)[CH2:6][CH:7]=[C:8]([CH3:11])[CH:9]=[CH2:10])[CH:3]=[O:4].C(=O)([O-])[O-].[Na+].[Na+].CO.[C:25]1([CH3:32])[C:26](C)=CC=[CH:29][CH:30]=1>>[CH3:11]/[C:8](/[CH2:7][CH2:6]/[CH:5]=[C:2](/[CH:3]=[O:4])\[CH3:15])=[CH:9]\[CH2:10]/[CH:26]=[C:25](/[CH:30]=[CH2:29])\[CH3:32]Participants
5
Procedure
Low boiling solvents may equally provide useful media whenever the reaction is effected at a pressure higher than the atmospheric pressure. For economical reasons xylene is preferred. It will be appreciated that the reaction time may vary within a wide range and depends particularly on the temperature chosen for carrying out the rearrangement. In a typical experiment 2,6-dimethyl-2-vinyl-3-isopropenyl-octa-5,7-dienal in xylene was heated at reflux for 40 min. under nitrogen. Sodium carbonate and methanol were added to the reaction mixture and the reaction mixture was further refluxed for 18 h while stirring. After dilution with pentane and drying over anhydrous sodium sulphate, the mixture was distilled to yield α-sinensal.
Workup
- temperatureat reflux for 40 min. under nitrogen
- temperaturethe reaction mixture was further refluxed for 18 h
- dry with materialAfter dilution with pentane and drying over anhydrous sodium sulphate
- distillationthe mixture was distilled
Sources & evidence
- ORD record
- ord-bf070ba14dc249b99146efe5c9a2429f
- Source dataset
- uspto-grants-1976_08
- Patent number
- US03974225
Reaction notes
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