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

HRID 1728289Notes

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.[I:21][C:22]1[CH:27]=[CH:26][C:25](O)=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+].IC1C=CC(OC(CCCCCCCC)C)=CC=1>CN(C=O)C>[I:21][C:22]1[CH:27]=[CH:26][C:25]([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])=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 80 °C

Procedure

The 2-methanesulfonyloxypentadecane (34.4 g, 102 mmol) was reacted with 4-iodophenol (22.7 g, 103 mmol) and potassium carbonate (14.3 g, 103 mmol) in DMF (200 ml) as per 2-(4-iodophenoxy)decane except that the temperature of the oil bath was maintained at 80° C. for 15 hrs and increased to 86° C. with stirring for an additional 24 hrs. At the end of this period, NMR spectral analysis indicated that the reaction was complete. The reaction mixture was processed as for 2-(4-iodophenoxy)decane except with four times the volumes to provide a light yellow oil. Flash column chromatography (silica, hexanes) yielded 2-(4-iodophenoxy)pentadecane (18.9 g, 43.0%) as a clear oil. Title Compound: 1H (300 MHz) and 13C (75 MHz) NMR spectra were consistent with the desired structure. FAB/MS: M+, 430. Calculated for C21H35IO: C, 58.47; H, 8.41; I, 29.42. Found: C, 58.91, H, 8.36; I, 29.26.

Workup

temperatureincreased to 86° C.
customto provide a light yellow oil

Sources & evidence

ORD record: ord-28320ca9118740db96c802fea6bf4a31
Source dataset: uspto-grants-1994_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05326553

Reaction notes

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