[OH:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[C:9]([C:11]1[CH:16]=[CH:15][C:14](O)=[CH:13][CH:12]=1)=[O:10].IC.[C:20](=[O:23])([O-])[O-].[K+].[K+].[CH3:26]C(C)=O>O>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:26])=[CH:4][C:3]=1[C:9]([C:11]1[CH:16]=[CH:15][C:14]([O:23][CH3:20])=[CH:13][CH:12]=1)=[O:10]A mixture of (2,5-dihydroxyphenyl)(4-hydroxyphenyl)methanone (1.8 g, 7.8 mmol), iodomethane (2.3 g, 16.4 mmol), potassium carbonate (5.4 g, 39 mmol) and acetone (25 mL) was heated to reflux. After 6 h, the reaction was cooled, poured into water and extracted with EtOAc. The organic layer was dried over MgSO4, concentrated and the crude product was purified by column chromatography (eluent 10% EtOAc/hexanes) to give a yellow solid (1.2 g, 60% yield, mp 70-72° C.); 1H NMR(DMSO-d8) 11.4 (s, 1H), 7.75 (d, 2H, J=8.5 Hz), 7.15-7.11 (m, 2H), 7.03-6.98 (m, 3H), 3.90 (s, 3H), 3.73 (s, 3H); MS m/e 257 (M−H)+.
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