[CH3:1][C:2]([C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[OH:11])=[O:3].[CH:12](=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[OH-].[Na+].OS(O)(=O)=O>O>[O:3]=[C:2]([C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[OH:11])[CH:1]=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=134.1 g of 5-chloro-2-hydroxyacetophenone and 22 g of benzaldehyde were added to a mixture of 180 ml of H2O and 37 g of 50% strength sodium hydroxide solution at room temperature. The mixture was heated to 55°-60° C., with thorough stirring, and was stirred at this temperature for about 1 hour. It was then rendered weakly acid with 25% strength H2SO4 (about 100 ml), with thorough cooling, and the precipitate was filtered off with suction, washed thoroughly with H2O and recrystallized from a 9:1 mixture of methanol and acetone to give 38.7 g of 3-oxo-1-phenyl-3-(2'-hydroxy-5'-chlorophenyl)-propene of melting point 88°-90° C.
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