Cl[CH2:2][C:3]1[CH:4]=[C:5]([O:13][CH3:14])[C:6]([O:11][CH3:12])=[CH:7][C:8]=1[CH2:9]Cl.[OH-].[Na+].[CH2:17]([NH2:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].C1(C)C=CC=CC=1>[CH2:17]([N:24]1[CH2:9][C:8]2[C:3](=[CH:4][C:5]([O:13][CH3:14])=[C:6]([O:11][CH3:12])[CH:7]=2)[CH2:2]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=12.35 g (10 mmol) of 4,5-bischloromethyl veratrol was added at room temperature to a suspension comprising 5 ml of a 50% sodium hydroxide aqueous solution, 25 ml of toluene, 1.25 g (11.66 mmol) of benzylamine and 0.2 g of a Starks catalyst. The mixture was stirred at room temperature for 20 hours, and then the organic layer was separated and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the crystalline residue was washed with isopropyl ether to obtain 1.87 g (yield: 70.0%) of the above identified compound as colorless needle-like crystals.
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