[OH-].[Na+].[OH:3][C:4]1[C:9]([CH:10]=[CH:11][CH3:12])=[CH:8][CH:7]=[CH:6][C:5]=1[C:13](=[O:16])[CH2:14][CH3:15].C(=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.Cl>C(O)C.O>[OH:3][C:4]1[C:9]([CH:10]=[CH:11][CH3:12])=[CH:8][CH:7]=[CH:6][C:5]=1[C:13](=[O:16])[CH:14]=[CH:15][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1
60 ml of 50% (w/v) sodium hydroxide was added dropwise during 30 minutes to a solution of 17.6 g of a 7:3 E-Z mixture of 2'hydroxy-3'-(1-propenyl)propiophenone (prepared as described in R. E. Ford. et al., J. Med. Chem., 29, 538, (1986)) and 10.82 g of benzaldehyde in 73 ml of ethanol stirred at 0° C. The temperature of the reaction mixture was raised to 25° C. and stirring was continued for 4 hours. After standing at room temperature overnight, 150 ml of water was added, followed by dropwise addition of 95 ml of 37% hydrochloric acid under stirring at 0° C. The precipitated solid was filtered by suction, washed with water and desiccated, yielding 26.8 g of 1-[2-hydroxy-3-(1-propenyl)phenyl]-3-phenyl-2-propen-1-one. This material was used without further purification in the next step.
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