[OH:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.Br[CH2:10][C:11]1[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[C:12]=1[C:13]([O:15][CH3:16])=[O:14].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH3:10][C:11]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][O:1][C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([OH:8])[CH:3]=2)[C:12]=1[C:13]([O:15][CH3:16])=[O:14]To a solution of 3-hydroxy-phenol (1.5 g, 13.6 mmol) in acetonitrile (50 mL) is added methyl 2-(bromomethyl)-6-methyl-benzoate (0.82 g, 3.4 mmol, example 2) followed by K2CO3 (3.76 g, 27.2 mmol). The resulting mixture is heated to 50° C. and stirred at this temperature for 90 min. then cooled, filtered and the filtrate concentrated under vacuum. The residue is purified by flash chromatography (silica, 5% ethyl acetate in dichloromethane) to give the title compound as a white solid. MS (EI) 272 (M+).
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