O[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:10])[CH3:9].[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])([O-])=[O:20].[K+].[K+]>CC(C)=O.CCOC(C)=O.O>[CH2:11]([O:20][CH2:9][C:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:2]=1)=[O:10])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1A mixture of 2′-hydroxyacetophenone (68.1 g, 0.500 mol), benzylbromide (65.4 ml, 94.1 g, 0.550 mol) and K2CO3 (103 g, 0.750 mol) in acetone (1.00L) was stirred and heated to reflux overnight. The resulting mixture was concentrated under reduced pressure to obtain a residue. The obtained residue was dissolved in the mixture of AcOEt and water and then extracted with AcOEt. The extract was washed with brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to give a crude material. The crude material was purified by distillation under reduced pressure to give starting compound 1A as a colorless oil (100 g, yield 88%).
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