O[CH:2]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[CH:13]=1)[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([OH:11])[CH:6]=1)=[O:4].OC1C=C(C(=O)C)C=CC=1.O.C(O)C>O.[Zn]>[OH:11][C:7]1[CH:6]=[C:5]([C:3](=[O:4])[CH2:2][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[CH:13]=2)[CH:10]=[CH:9][CH:8]=12-Hydroxy-1,2-bis(3-hydroxyphenyl)ethanone was reduced by the procedure of M. Pisova and M. Soncek [Coll. Czech, Chem. Comm., 38, 3876 (1973)]. A mixture of 2-hydroxy-1,2-bis(3-hydroxyphenylethanone (18 g.) chromic sulfate hydrate (20.9% Cr; 60 g.), zinc dust (49 g.) and water-ethanol (1:1, 1 liter) was stirred under an atmosphere of nitrogen for 11 hours. The mixture was diluted with water and extracted with three portions of ethyl acetate. The organic solution was washed with saturated brine solution and dried over magnesium sulfate. The solution was concentrated and the product crystallized from ethyl acetate-benzene (seeding); yield: 8.51 g., m.p. 155°-156°.
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