[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=[O:6].[CH3:12][O:13][CH2:14][CH2:15][CH2:16]Br.C(=O)([O-])[O-].[K+].[K+].O>C(#N)C.C(OCC)(=O)C>[CH3:11][O:10][C:9]1[CH:8]=[CH:7][C:4]([CH:5]=[O:6])=[CH:3][C:2]=1[O:1][CH2:16][CH2:15][CH2:14][O:13][CH3:12]
3-hydroxy-4-methoxybenzaldehyde (15 g, 98.6 mmol) was dissolved in acetonitrile (200 mL). 1-Methoxy-3-bromopropane (16.6 g, 108 mmol) and potassium carbonate (34 g, 247 mmol) were added and the mixture was brought to reflux and stirred for 3 hrs. After cooling to room temperature, water and ethyl acetate were added. The aqueous layer was extracted three times with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to yield 22 g (quantitative yield) of the desired product as a yellow oil, used without further purification.
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