Sodium Iodide → HCID 54421864, compound

Reaction equation

Br[CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][C:7]=1[O:14][CH3:15].C(=O)([O-])[OH:17].[Na+].[I-].[Na+]>CS(C)=O>[CH3:15][O:14][C:7]1[CH:8]=[C:9]([O:12][CH3:13])[CH:10]=[CH:11][C:6]=1[CH2:5][CH2:4][CH2:3][CH:2]=[O:17]

Participants

Procedure

A mixture of 1-(4-bromobutyl)-2,4-dimethoxybenzene (11.0 g, 40.2 mmol), sodium hydrogen carbonate (6.75 g, 80.3 mmol) and sodium iodide (9.03 g, 60.2 mmol) in DMSO (80 mL) was stirred at 105 C. for 1.5 h. The reaction mixture was allowed to cool to some extent after which ice water (240 mL) was added. The mixture was extracted with diethyl ether (2×200 mL), washed with brine (50 mL), dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography (SiO2, hexane-EtOAc, 80:20) yielding the title compound as a colorless liquid (3.56 g): 1H NMR (CDCl3 -d) 9.74 (t, J=1.8 Hz, 1H), 7.00 (d, J=7.9 Hz, 1H), 6.45-6.40 (m, 2H), 3.79 (s, 3H), 3.79 (s, 3H), 2.59 (t, J=7.4 Hz, 2H), 2.44-2.39 (m, 2H), 1.90 (quintet, J=7.4 Hz, 2H); 13C NMR (CDCl3 -d) 202.91, 159.32, 158.28, 130.14, 121.90, 103.78, 98.44, 55.28, 55.16, 43.25, 28.80, 22.50; MS (EI, 70 eV): m/z (rel. int.) 208 (M+, 31), 164 (44), 151 (100), 121 (76), 91 (16).