[Cl:1][C:2]1[C:3](O)=[C:4]([O:11][CH3:12])[CH:5]=[C:6]([CH:10]=1)C(O)=O.[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[C:22](=[O:25])([O-])[O-:23].[K+].[K+].C(O[CH2:32][CH3:33])(=O)C.CN([CH:37]=[O:38])C>O>[CH2:14]([O:23][C:22](=[O:25])[C:6]1[CH:5]=[C:4]([O:11][CH3:12])[C:3]([O:38][CH2:37][C:33]2[CH:32]=[CH:6][CH:10]=[CH:2][CH:3]=2)=[C:2]([Cl:1])[CH:10]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1A mixture of 5-chloro-vanillic acid (4.05 g, 20 mmol), benzyl bromide (8.55 g, 50 mmol) and potassium carbonate (6.90 g, 50 mmol) in DMF (60 mL) was stirred at room temperature for 18 hours. The mixture was transferred into a separation funnel and ethyl acetate (100 mL) and water (100 mL) were added, the organic layer was separated, washed with water (2×50 mL) and brine (50 mL), dried over sodium sulphate and concentrated under reduced pressure. The residue was crystallised from dichloromethane/hexane. Yield: 7.34 g (96%) colourless needles. 1H-NMR (400 MHz, CDCl3) δ 3.92 (s, 3H, —OCH3), 5.13 (s, 2H), 5.36 (s, 2H), 7.31-7.51 (m, 10H), 7.53 (d, J=2.0 Hz, 1H), 7.73 (d, J=2.0 Hz, 1H). LRMS (FAB+): 91.0 (100), 382.1 (15, [M+H]+).
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