4-Iodophenol → 2-(4-Iodophenoxy)-undecane

HRID 1728287Notes

Reaction equation

I[C:2]1C=CC(O)=CC=1.C(=O)([O-])[O-].[K+].[K+].[I:15][C:16]1[CH:32]=[CH:31][C:19]([O:20][CH:21]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH3:22])=[CH:18][CH:17]=1>CN(C=O)C>[I:15][C:16]1[CH:32]=[CH:31][C:19]([O:20][CH:21]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:2])[CH3:22])=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 84 °C

Procedure

The above product (31.3 g, 136.7 mmol) was reacted with 4-iodophenol (30.1 g, 136.8 mmol), and potassium carbonate (18.9 g, 136.7 mmol) in DMF (270 ml) at 80° C. as for 2-(4-iodophenoxy)decane. After stirring for 13 hrs, the reaction was analyzed by 1H NMR indicating that the reaction was about 66% complete. The temperature of the oil was increased 84° C. After an additional 34 hrs, 1H NMR spectral analysis indicated that the reaction was complete. The reaction was processed as for 2-(4-iodophenoxy)-decane except at 2 times the volume to give a light yellow oil. This product was further purified by flash column chromatography (silica, hexanes) to give 2-(4-iodophenoxy)-undecane (16.1 g, 31%) as a clear oil. Title Compound: 1H (300 MHz) and 13C (75 MHz) NMR spectra were consistent with the desired structure. FAB/MS: M+, 374. Calculated for C17H27IO: C, 54.55; H, 7.27; I, 33.90. Found: C, 54.75, H, 7.32; I, 33.97.

Workup

waitAfter an additional 34 hrs
customto give a light yellow oil
customThis product was further purified by flash column chromatography (silica, hexanes)

Sources & evidence

ORD record: ord-c4e4312adb294e25b5cc8b5a38fefd2e
Source dataset: uspto-grants-1994_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05326553

Reaction notes

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