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

HRID 974743

Reaction equation

HRID 974743 reaction equation
CS(OC(CCCCCCC)C)(=O)=O.C1C(I)=CC(I)=C(O)C=1I.C(=O)([O-])[O-].[K+].[K+].[I:31][C:32]1[CH:53]=[C:52]([I:54])[CH:51]=[C:50]([I:55])[C:33]=1[O:34][CH:35]([CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43]CCCCCC)[CH3:36]>CN(C=O)C>[I:31][C:32]1[CH:53]=[C:52]([I:54])[CH:51]=[C:50]([I:55])[C:33]=1[O:34][CH:35]([CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH3:36]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 118622,4,6-TriiodophenolHCID 149160062-MethanesulfonyloxynonaneHCID 153433092-(2,4,6-Triiodophenoxy)pentadecane2×

Product 1

HCID 153433132-(2,4,6-Triiodophenoxy)nonaneYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The 2-methanesulfonyloxynonane (22.8 g, 102 mmol), triiodophenol (48.8 g, 103 mmol) and potassium carbonate (14.2 g, 103 mmol) were reacted in DMF (206 ml) as per 2-(2,4,6-triiodophenoxy)pentadecane except at an oil bath temperature of 82° C. for 14 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 2-(2,4,6-triiodophenoxy)nonane (40.8 g, 68.0%).

Workup

  1. customto provide a light brown oil

Sources & evidence

ORD record
ord-5924d4a5d885450cb80faddba131a647
Source dataset
uspto-grants-1997_03
Patent number
US05607660

Linked notes

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