[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([OH:8])[C:3]=1[C:9](=[O:11])[CH3:10].[OH2:12].[C:13]1(C)C=[CH:17][C:16](S(O)(=O)=O)=[CH:15][CH:14]=1>O1CCOCC1.O1C=CCCC1.C(OCC)C>[OH:1][C:2]1[C:3]([C:9](=[O:11])[CH3:10])=[C:4]([O:8][CH:17]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)[CH:5]=[CH:6][CH:7]=12′,6′-Dihydroxyacetophenone (5.0 g) was dissolved in dioxane (20 mL) and 3,4-dihydro-2H-pyran (16 mL). To the solution was added p-toluenesulfonic acid monohydrate (0.21 g), and the mixture was stirred at room temperature for 1.5 hours. The reaction mixture was diluted with diethyl ether, and the mixture was washed with 5% aqueous potassium carbonate solution. The organic layer was extracted with 2 mol/L aqueous sodium hydroxide solution, and the aqueous layer was neutralized until pH was about 8. The resulting mixture was extracted with diethyl ether. The organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate to give the title compound (5.64 g).
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