Geranylgeraniol → 3,7,11,15-tetramethyl-2E,6E,10E,14-hexadecatetraenal

HRID 1899794Notes

Reaction equation

HRID 1899794 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

HCID 5281365Geranylgeraniol

Product 1

HCID 117812093,7,11,15-tetramethyl-2E,6E,10E,14-hexadecatetraenal

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

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.

Workup

  1. customThe solids were removed by filtration through a pad of celite
  2. washwashing with methylene chloride (50 ml)
  3. customThe resulting solution was evaporated in vacuo

Sources & evidence

ORD record
ord-31bc3dc820fe43bfb9fec1f0c7fb58d9
Source dataset
uspto-grants-1996_11
Patent number
US05574025

Reaction notes

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