Triethylamine → 1-(2,4,6-Triiodophenoxy)-3,7-dimethyl-6-octene

HRID 1728291Notes

Reaction equation

HRID 1728291 reaction equation
[CH3:1][C:2](=[CH:4][CH2:5][CH2:6][CH:7]([CH2:9][CH2:10][OH:11])[CH3:8])[CH3:3].C(N(CC)CC)C.CS(Cl)(=O)=O.[I:24][C:25]1[CH:30]=[C:29]([I:31])[CH:28]=[C:27]([I:32])[C:26]=1O.C(=O)([O-])[O-].[K+].[K+]>ClCCl.CN(C)C=O.O>[I:24][C:25]1[CH:30]=[C:29]([I:31])[CH:28]=[C:27]([I:32])[C:26]=1[O:11][CH2:10][CH2:9][CH:7]([CH3:8])[CH2:6][CH2:5][CH:4]=[C:2]([CH3:3])[CH3:1]

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 8842CitronellolHCID 11430Potassium CarbonateHCID 118622,4,6-TriiodophenolHCID 31297Methanesulfonyl chloride

Product 1

HCID 153433281-(2,4,6-Triiodophenoxy)-3,7-dimethyl-6-octeneYield 15%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
100 °C

Procedure

To a stirred solution of citronellol (4.5 g, 28.8 mmol) and triethylamine (5.2 ml, 34.6 mmol, 1.2 eq) in dichloromethane (50 ml) cooled to 0° C. was added dropwise, a solution of methanesulfonyl chloride (2.46 ml, 28.8 mmol) in dichloromethane (50 ml). The solution was stirred for 1 hr. at 0° C. under nitrogen and then water was added. The dichloromethane layer was dried over magnesium sulfate after washing with saturated aqueous sodium chloride and then concentrated in vacuo to give an oil. 1H-NMR (300 MHZ) spectrum of the oil indicated the desired methanesulfonate ester. The methanesulfonate ester was added to a stirred mixture of 2,4,6-triiodophenol (13.6 g, 28.8 mmol) and potassium carbonate (4.0 g, 28.8 mmol) in dimethylformamide (50 ml). The mixture was heated to 100° C. for 30 minutes and cooled to room temperature. The crude product was isolated by partitioning the reaction mixture between water and dichloromethane. The organic layer was concentrated under vacuum to give an oil. The oil was purified by flashing through basic alumina with hexanes to give the desired product in 15% yield as a light-sensitive oil. Title Compound: 1H (300 MHz) and 13C (75 MHz) NMR spectra were consistent with the desired structure. Calculated for C16H21I3O: C, 31.50; H, 3.47; I, 62.41. Found: C, 31.71; H, 3.41; I, 62.30.

Workup

  1. additionwas added dropwise
  2. dry with materialThe dichloromethane layer was dried over magnesium sulfate
  3. washafter washing with saturated aqueous sodium chloride
  4. concentrationconcentrated in vacuo
  5. customto give an oil
  6. temperaturecooled to room temperature
  7. customThe crude product was isolated
  8. customby partitioning the reaction mixture between water and dichloromethane
  9. concentrationThe organic layer was concentrated under vacuum
  10. customto give an oil
  11. customThe oil was purified

Sources & evidence

ORD record
ord-84eefa116e1942029c940734a825f1d1
Source dataset
uspto-grants-1994_07
Patent number
US05326553

Reaction notes

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