Reaction equation
[CH:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][CH:4]=1)=[CH2:2].[CH2:11]([OH:14])[CH2:12][CH3:13].[C:15]1(C)[CH:20]=CC(S(O)(=O)=O)=C[CH:16]=1.[OH-].[Na+]>C1C=CC=CC=1.CCOCC.O>[CH:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]([O:14][CH2:11][CH2:12][CH3:13])[O:8][CH2:16][CH2:15][CH3:20])=[CH:5][CH:4]=1)=[CH2:2]Participants
8
Procedure
In a 100 ml 3-necked round-bottomed flask, 6.8 g (51.5 mmol) of 4-vinylbenzaldehyde, 12.4 g (205.8 mmol) of n-propanol and 0.1 g (0.5 mmol) of p-toluenesulfonic acid are dissolved in 45 ml of benzene. The solution is refluxed for 22 hours using a water separator and then ether is added thereto. The mixture is subsequently neutralised with 0.1N sodium hydroxide solution. The organic phase is then washed three times with water, dried over magnesium sulfate and concentrated. The resulting oil can be purified by column chromatography (stationary phase silica gel, mobile phase hexane/ether 5/4) to yield 2.54 g (10.8 mmol, 21% of the theoretical yield) of the desired substance in the form of a clear oil.
Workup
- temperatureThe solution is refluxed for 22 hours
- washThe organic phase is then washed three times with water
- dry with materialdried over magnesium sulfate
- concentrationconcentrated
- customThe resulting oil can be purified by column chromatography (stationary phase silica gel, mobile phase hexane/ether 5/4)
- customto yield 2.54 g (10.8 mmol, 21% of the
- customtheoretical yield) of the desired substance in the form of a clear oil
Sources & evidence
- ORD record
- ord-ae10a3d48b63427d8c466b82ddd5b310
- Source dataset
- uspto-grants-1993_12
- Patent number
- US05274060
Linked notes
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