油脂の酸化防止に関する研究-7-

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In the present paper, several ω, ω'-(3, 4-dihyhroxyphenyl) alkanes were synthesized to find the relation between the chemical structure and antioxidant property as well as in the previous pape(1). 4-Iodoveratrol (I) was prepared by the treatment of veratrol with iodine and mercuric oxide. Heating of (I) with Cu powder in C02 gave 3, 4, 3', 4'-tetramethoxybiphenyl (II), which was demethylated with HI to yield 3, 4, 3', 4'-tetrahydroxydbiphenyl (III), mp. 225_??_227°. Veratroyl chloride was condensed with veratrol in the presence of A1C13 to give veratroylveratrol (IV), which was reduced with Na-alcoholate to 3, 4, 3', 4'-tetramethoxybiphenylmethane (V), mp. 70°. Demethylation of (V) with HI gave 3, 4, 3', 4'-tetrahydroxybiphenylmethane (VI), mp. 145°. It-had been reported by CARO(4) that 3, 4, 3', 4'-tetrahydroxybiphenylmethane, mp. 220 (decompn.) was obtained when a solution of 5 parts of catechol in 50 parts of H2O was boiled with 40% HCHO solution and a few drops of HC1 or H2S04. This experiment was repeated by the authors in various conditions, but such a compound was never obtained. Therefore, it should be conclued that CARD's report concerned with (VI) is errornous. Diveratralacetone (VI) prepared from veratric aldehyde and acetone in NaOH solution was reduced by the catalytic hydrogenation and CLEMMENSEN reduction successively, and demethyl-ation of the resulting product with HI gave 1, 5-bis-(3, 4-dihydroxyphenyl) pentane(X), mp. 128_??_129°. 1, 8-Diveratroyloctane (XI), mp. 106_??_107°, the intermediate for the. preparation of 1, 10-bis-(3, 4-dihydroxyphenyl) decane was obtained by the treatment of sebacyl chloride with veratrol in the presence of AlC13, instead of the condensation of . sebacic polyanhydride with veratrol(1). The authors wish to express their appreciation to Professor Dr. Y SUMIKI for his guidance and advice.
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油脂の酸化防止に関する研究-7-

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