Potassium Carbonate → 3-(2,4,6-Triiodophenoxy)nonane

HRID 53484

Reaction equation

HRID 53484 reaction equation
S([O-])(=O)(=O)C.[CH3:6][CH2:7][CH:8]([OH:15])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[CH:16]1[C:17]([I:25])=[CH:18][C:19]([I:24])=[C:20](O)[C:21]=1[I:22].C(=O)([O-])[O-].[K+].[K+].IC1C=C(I)C=C(I)C=1OC(CCCCCCCCCCCCC)C>CN(C=O)C>[I:22][C:21]1[CH:20]=[C:19]([I:24])[CH:18]=[C:17]([I:25])[C:16]=1[O:15][CH:8]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH2:7][CH3:6]

Participants

7

Reactant 5

HCID 11430Potassium CarbonateHCID 118622,4,6-TriiodophenolHCID 122163-NonanolHCID 85257MethanesulfonateHCID 153433092-(2,4,6-Triiodophenoxy)pentadecane2×

Product 1

HCID 199598483-(2,4,6-Triiodophenoxy)nonaneYield 67.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The mesylate of 3-nonanol (11.5 g, 51.9 mmol), triiodophenol (24.5 g, 51.9 mmol) and potassium carbonate (7.18 g, 51.9 mmol) were reacted in dry DMF (200 ml) as per 2-(2,4,6-triiodophenoxy)-pentadecane except at an oil bath temperature of 87° C. for 16 hrs. The reaction was processed as for 2-(2,4,6-triiodophenoxy)-pentadecane to provide a light brown oil. Flash column chromatography (silica, hexanes) provided 3-(2,4,6-Triiodophenoxy)-nonane (20.9 g, 67%) as a clear viscous oil.

Workup

  1. customto provide a light brown oil

Sources & evidence

ORD record
ord-0bddb144ab1d491b81ab3a9d61a86613
Source dataset
uspto-grants-1997_04
Patent number
US05620677

Linked notes

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