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

HRID 1728282Notes

Reaction equation

HRID 1728282 reaction equation
CS(OC(CCCCCCCC)C)(=O)=O.IC1C=C(I)C=C(I)C=1O.C(=O)([O-])[O-].[K+].[K+].[I:32][C:33]1[CH:54]=[C:53]([I:55])[CH:52]=[C:51]([I:56])[C:34]=1[O:35][CH:36]([CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45]CCCCC)[CH3:37]>CN(C=O)C>[I:32][C:33]1[CH:54]=[C:53]([I:55])[CH:52]=[C:51]([I:56])[C:34]=1[O:35][CH:36]([CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])[CH3:37]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 118622,4,6-TriiodophenolHCID 14916009Decan-2-yl methanesulfonateHCID 153433092-(2,4,6-Triiodophenoxy)pentadecane2×

Product 1

HCID 153433102-(2,4,6-Triiodophenoxy)-decaneYield 75.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The 2-methanesulfonyloxydecane (14.8 g, 62.6 mmol), 2,4,6-triiodophenol (29.7 g) 62.9 mmol) and potassium carbonate (8.7 g, 63.0 mmol) were reacted in DMF (210 ml) as per 2-(2,4,6-triiodophenoxy)-pentadecane except at an oil bath temperature of 72° C. for 88 hrs. The reaction was processed as for 2-(2,4,6-triiodophenoxy)-pentadecane to provide a light brown residue. Flash column chromatography (silica, hexanes) provided 2-(2,4,6-triiodophenoxy)-decane (29.1 g, 75.9%) as a white solid. Title Compound: 1H (300 MHz) and 13C (75 MHz) NMR spectra were consistent with the desired structure. Calculated for C16H23I3O: C, 31.40; H, 3.79; I, 62.20. Found: C, 31.50, H, 3.75; I, 62.37.

Workup

  1. customto provide a light brown residue

Sources & evidence

ORD record
ord-7b98454e9a4d4205a8dd7eb705c9dc1b
Source dataset
uspto-grants-1994_07
Patent number
US05326553

Reaction notes

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