Geranylgeraniol → 3,7,11,15-tetramethyl-2E,6E,10E,14-hexadecatetraenal
Reaction equation
[CH3:1]/[C:2](/[CH2:6][CH2:7]/[CH:8]=[C:9](\[CH3:21])/[CH2:10][CH2:11]/[CH:12]=[C:13](\[CH3:20])/[CH2:14][CH2:15][CH:16]=[C:17]([CH3:19])[CH3:18])=[CH:3]\[CH2:4][OH:5]>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH3:1]/[C:2](/[CH2:6][CH2:7]/[CH:8]=[C:9](\[CH3:21])/[CH2:10][CH2:11]/[CH:12]=[C:13](\[CH3:20])/[CH2:14][CH2:15][CH:16]=[C:17]([CH3:19])[CH3:18])=[CH:3]\[CH:4]=[O:5]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of (E,E,E)-3,7,11,15 tetramethyl-2,6,10,14-hexadecatetraen-1-ol (320 mg, 1.1 mmol) in dry methylene chloride (10 ml) at room temperature was added manganese dioxide (957 mg, 0.011 mol) and the resulting mixture stirred for 16 hours. The solids were removed by filtration through a pad of celite washing with methylene chloride (50 ml). The resulting solution was evaporated in vacuo to afford the aldehyde (1) as a clear colorless oil.