[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.[C:12]1([CH3:20])[CH:17]=[CH:16][C:15]([CH:18]=O)=[CH:14][CH:13]=1.[OH-:21].[Na+].OO.Cl>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:11][C:20]([C:12]3[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=3)=[C:9]([OH:21])[C:8](=[O:10])[C:6]=2[CH:7]=1
A 8.5 g quantity of 5'-chloro-2'-hydroxyacetophenone and 6.0 g of p-tolualdehyde were dissolved in 105 ml of ethanol. Then 17 ml of an aqueous solution containing 10 g of sodium hydroxide was slowly added thereto dropwise and stirred at room temperature for 4 hours. Then 350 ml of ethanol and 17 ml of an aqueous solution containing 3.5 g of sodium hydroxide were added to the reaction mixture, and 8.3 ml of a 30% aqueous hydrogen peroxide solution was further added dropwise slowly and stirred at room temperature for 12 hours. A 10% aqueous HCl solution was added to adjust the reaction mixture to pH 3. The crystals precipitated were collected by filtration and washed serially with 10 ml of water, 5 ml of ethanol and 10 ml of diethyl ether, thus giving 6.0 g of 6-chloro-3-hydroxy-2-(4-methylphenyl)-4H-1-benzopyran-4-one as crystals.
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