[CH2:1]([OH:10])/[CH:2]=[CH:3]\[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]>CCOCC.[O-2].[O-2].[Mn+4]>[CH:1](=[O:10])/[CH:2]=[CH:3]\[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]Cis-2-nonenol (5 g, mole) is stirred with manganese dioxide (50 g, mole) in ether (250 ml) at room temperature for 1 hour. The mixture is filtered, ether removed, and the residue distilled to give cis-2-nonenal.
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