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]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, 1 H), 7.00 (d, J=7.9 Hz, 1 H), 6.45-6.40 (m, 2 H), 3.79 (s, 3 H), 3.79 (s, 3 H), 2.59 (t, J=7.4 Hz, 2 H), 2.44-2.39 (m, 2 H), 1.90 (quintet, J=7.4 Hz, 2 H); 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).
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