[CH:1]([C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[OH:14])[C:6]([O:8][CH2:9][CH3:10])=[O:7])=O.Br[CH2:16][C:17](=[O:19])[CH3:18].C(=O)([O-])[O-].[K+].[K+].O>C(#N)C>[C:17]([C:18]1[O:14][C:13]2[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=2[CH:1]=1)(=[O:19])[CH3:16]To a solution of ethyl 3-formyl-4-hydroxybenzoate (4.00 g, 11.5 mmol) in acetonitrile (85 mL) were added bromoacetone (9.68 g, 64.1 mmol) and potassium carbonate (14.7 g, 106 mmol), and the mixture was stirred at 70° C. overnight. Water was added to the reaction mixture, and the mixture was extracted twice with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solution was passed through silica gel. The solvent was evaporated under reduced pressure, and the obtained solid was washed with diisopropyl ether to give the title compound (6.59 g, yield 67%).
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