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

HRID 1034380Notes

Reaction equation

CS([O:5][CH:6]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH3:7])(=O)=O.[CH:21]1[C:22]([I:30])=[CH:23][C:24]([I:29])=[C:25](O)[C:26]=1[I:27].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[I:27][C:26]1[CH:25]=[C:24]([I:29])[CH:23]=[C:22]([I:30])[C:21]=1[O:5][CH:6]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH3:7]

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of 2-methanesulfonyloxypentadecane (15.5 g, 48.1 mmol) in dry DMF (200 ml) was added triiodophenol (22.6 g, 47.9 mmol) and potassium carbonate (6.6 g, 47.8 mmol). The reaction flask was immersed in an oil bath which was heated to 85° C. over a period of 0.5 hr. The reaction was stirred under N2 atmosphere for 16 hrs. At the end of this period the reaction was processed as for Example 1 except at 4 times the volumes to provide a brown residue. Flash column chromatography (silica, hexanes) provided 2-(2,4,6-triiodophenoxy)pentadecane (19.2 g, 58.8%) as a white solid. Mp: 56°-58° C. p Title Compound:1H (300 MHz) and 13C (75 MHz) NMR spectra were consistent with the desired structure. Calculated for C21H33I3O: C, 36.97; H, 4.88; I, 55.81. Found: C, 36.89, H, 4.80; I, 55.85.

Workup

customThe reaction flask was immersed in an oil bath
customto provide a brown residue

Sources & evidence

ORD record: ord-b9d4227e698b4257ba8ccb50b7a302f4
Source dataset: uspto-grants-1994_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05316755

Reaction notes

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