[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].BrC[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][C:12]=1[O:19][CH3:20].[C:21](=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1>CC(C)=O>[CH3:18][O:17][C:14]1[CH:15]=[C:16]([CH:11]=[C:12]([O:19][CH3:20])[CH:13]=1)[CH2:21][O:2][C:1]1[CH:3]=[C:4]([OH:5])[CH:6]=[CH:7][CH:8]=1Resorcinol (0.21 g, 1.87 mmol), 4-bromomethyl-1,3-dimethoxybenzene (0.39 g, 1.70 mmol), potassium carbonate (0.26 g, 1.87 mmol) and 18-crown-6-ether (0.09 g, 0.34 mmol) were stirred together in acetone (15 cm3, 99%) under nitrogen at room temperature for 20 hours. The solution was evaporated under reduced pressure, and the residue was taken up in dichloromethane (10 cm3) and water (10 cm3). The aqueous layer was extracted with dichloromethane (2×10 cm3), and the combined extracts were washed with water (2×20 cm3), dried (MgSO4), and evaporated under reduced pressure. The residue was chromatographed (SiO2, dichloromethane) to give the phenol, (0.12 g, 27%), as an oil.
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