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Ⅴ.3,5-二甲氧基-4-羧基-隣苯二甲酸酐的合成

Ⅴ. SYNTHESIS OF 3,5-DIMETIIOXY-4-CARBOXYPHTHALIC ANHYDRIDE

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【作者】 黄耀曾; 涂通源; 戴立信;

【Author】 HUANG YAO-TSENG, TU TCNG-YUAN and TAI LI-HSIN. (Institute of Organtic Chemistry, Academia Sinica)

【机构】 中国科学院有机化学研究所; 中国科学院有机化学研究所;

【摘要】 本文报导3,5-二甲氧基-4-羧基-隣苯二甲酸酐(Ⅰ)的合成。

【Abstract】 The title compound was prepared from orcinol by six stages of reactions, p- Orcellinic aeid (Ⅳ), prepared from orcinol according to Robertson and Robinson,was esterified to give its methyl ester (Ⅴ) which on formylation by Gattermannaldehyde synthesis afforded methyl 2, 6-dihydroxy-3-formyl-4-methyl-benzoate (Ⅵ),m. p. 147--148°, in 95% yield. Methylation of the latter gave rise to 2, 6-dimethoxy-3-formyl-4-methyl-benzoate (Ⅶ), m. p. 95--97°. Oxidation of (Ⅶ) with pota-ssium permanganate in water solution produced methyl 2, 6 dimethoxy 3-carboxy4-methyl-benzoate (o), m. p. 123--124°, while in alkaline medium produced twocompounds: 3, 5-dimethoxy-trimellitic acid (Ⅷ), m. p. 234--235°, and 2, 6-dime-thoxy-4-methyl-isophthalic acid (Ⅸ), m. p. 210--212°. Eithor (Ⅹ) or (Ⅸ) couldbe further oxidized to (Ⅷ). The anhydride, 3, 5-dimethoxy-4-carboxy-phthalicanhydride was finally obtained by treating (Ⅷ) with acetic anhydride as colorlesscrystals, m. p. 232--234°.

  • 【文献出处】 化学学报 ,Acta Chimica Sinica , 编辑部邮箱 ,1958年04期
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