COC[O:4][C:5]1[CH:28]=[C:27]([O:29]COC)[CH:26]=[CH:25][C:6]=1[C:7](=[O:24])[CH:8]=[CH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16]COC)=[C:12]([O:20]COC)[CH:11]=1>Cl.CO>[OH:4][C:5]1[CH:28]=[C:27]([OH:29])[CH:26]=[CH:25][C:6]=1[C:7](=[O:24])[CH:8]=[CH:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([OH:20])[CH:11]=1Then, 4.0 g of the so-obtained 2',3,4,4'-tetrakis(methoxymethoxy)chalcone was dissolved in 36 ml of a hydrochloric acid/methanol reagent, and the solution was refluxed for 10 minutes. The reaction liquid was poured into ice water, and the precipitated crystal was recovered by filtration, washed with water, dried and subjected to the column chromatograpy 280 g of 230-400 mesh Kieselgel, eluting solvent=hexane/ethyl acetate (1/1), 0.4 kg/cm2). Fractions of 50 ml were collected, and the 32th to 70th fractions were combined to obtain 543.2 mg (yield=22.1%) of 2',3,4,4'-tetrahydroxychalcone.
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