Water → (E)-1-(2,4,6-triiodophenoxy)-3,7-dimethyl-2,6-octadiene

HRID 1034395Notes

Reaction equation

HRID 1034395 reaction equation
[CH:1]1[C:2]([I:10])=[CH:3][C:4]([I:9])=[C:5]([OH:8])[C:6]=1[I:7].C(=O)([O-])[O-].[K+].[K+].[CH2:17](Br)/[CH:18]=[C:19](/[CH2:21][CH2:22][CH:23]=[C:24]([CH3:26])[CH3:25])\[CH3:20].O>CN(C)C=O>[I:7][C:6]1[CH:1]=[C:2]([I:10])[CH:3]=[C:4]([I:9])[C:5]=1[O:8][CH2:17]/[CH:18]=[C:19](\[CH3:20])/[CH2:21][CH2:22][CH:23]=[C:24]([CH3:26])[CH3:25]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 118622,4,6-TriiodophenolHCID 53658672,6-Octadiene, 1-bromo-3,7-dimethyl-, (2E)-

Product 1

HCID 15343331(E)-1-(2,4,6-triiodophenoxy)-3,7-dimethyl-2,6-octadieneYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of triiodophenol (10.0 g, 21.2 mmol), milled potassium carbonate (3.1 g, 22.5 mmol, 1.06 eq) and geranyl bromide (4.0 ml, 20.2 mmol) in dimethyl formamide (25 ml) was heated to 50° C. for 2 hrs and cooled. The mixture was poured into 300 ml of water and extracted with ethyl acetate. The ethyl acetate extract was filtered through a short pad of silica gel, then alumina, eluting with ethyl acetate-hexanes (1:1). The eluent was concentrated under high vacuum to give the product in 87% yield as an oil.

Workup

  1. temperaturecooled
  2. extractionextracted with ethyl acetate
  3. extractionThe ethyl acetate extract
  4. filtrationwas filtered through a short pad of silica gel
  5. washalumina, eluting with ethyl acetate-hexanes (1:1)
  6. concentrationThe eluent was concentrated under high vacuum
  7. customto give the product in 87% yield as an oil

Sources & evidence

ORD record
ord-00ecf69256e0426d9c8d6032f79bdc37
Source dataset
uspto-grants-1994_05
Patent number
US05316755

Reaction notes

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