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sanko211荣誉版主 (职业作家)
小木虫扣篮王
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200金币求3-醛基水杨酸合成方法
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200金币求3-醛基水杨酸合成方法，不要求提供文献，只要方法就可以了 |
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doctorzhjw
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sanko211(金币+30,VIP+0):先拿来看看 3-31 16:50
sanko211(金币+30,VIP+0):先拿来看看 3-31 16:50
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1、1932年的J.Chem.Soc. 1987页“273. Reactions between Hexameth ylenetetramine and Phenolic Compounds. Part I. A New Method for the Preparation of 3- and 5-Aldehydosalicylic Acids。” By J. C. DUFF and E. J. Bms. 40克水杨酸得到3.3克3-醛基水杨酸 2、1934年的J.Chem.Soc. 1305页“282. Reactions between hexamethylenetetramine and phenolic compounds. Part II. Formation of phenolic aldehydes. Distinctive behaviour of p-nitrophenol。” By J. C. Duff, E. J. Bills. 10克水杨酸得到1.1克3-醛基水杨酸 3、1940年的J.Am.Chem.Soc. 62卷890页“Proof of Structure of 6-Chloro-8-chlorornethyl-l,3-benzodioxane by Oxidation。” BY C. A. BUEHLERB, . CALVINB ASS,R OBERTB . DARLINGAN D MILTONE . LUBS 90克水杨酸得到3克3-醛基水杨酸 4、1952年的J.Org.Chem. 17卷1252页“Photobromination of Substituted Toluenes as a Route to Substituted Benzyl Alcohols and Benzaldehydes。” Ernest L. Eliel, Donald E. Rivard 以邻甲基水杨酸为原料能获得3-醛基水杨酸38%的产率 以上1和2为Duff法，99%的文献是参考这一方法来合成3-醛基水杨酸的，3为Reimer-Tiemann法，4为溴化法，其它各种甲酰化方法还有Gattermann-Koch法、Gattermann法、二氯甲基醚法和Vilsmeier法等。 |
4楼2009-03-31 14:36:56
2楼2009-03-31 13:58:27
lionwick
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sanko211(金币+1,VIP+0):我先看看 3-31 16:42
sanko211(金币+15,VIP+0):先拿来看看 3-31 16:46
sanko211(金币+1,VIP+0):我先看看 3-31 16:42
sanko211(金币+15,VIP+0):先拿来看看 3-31 16:46
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http://www.damipan.com/file/JRsjjA.html 你去下载吧。Scifinder 出来的。 |
3楼2009-03-31 14:23:11
jingweiii
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sanko211(金币+35,VIP+0):请问你所说的改进方法是可以的吗，另外最后一步中沉淀指的是3-醛基水杨酸吗？ 4-1 08:27
sanko211(金币+35,VIP+0):请问你所说的改进方法是可以的吗，另外最后一步中沉淀指的是3-醛基水杨酸吗？ 4-1 08:27
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3-醛基水杨酸的制备(改进） 水杨酸（15克）六次甲基四胺（15克）溶于60ml冰醋酸中，在110°C油浴加热回流6小时，热溶液与120ml沸水和75ml浓盐酸混合，搅拌10min，冰浴得到黄色沉淀，抽滤。 干燥固体，碾碎。用苯在索氏提取器浸取固体10小时。所得苯溶液减压蒸馏除苯，得淡黄固体，在50℃下溶解于75ml 3M-NH3.H2O，加入37.5ml 10% BaCl2，和18.75ml 2M-NaOH。2小时后，收集3-醛基水杨酸钡沉淀，用稀盐酸分解（转变为酸），所得沉淀在沸水中重结晶得到3.3克的3-醛基水杨酸。 原文献： 273. Reactions between Hexamethylenetetramine and Phenolic Compounds. Part I. A New Method for the Preparation of 3-and 5-Aldehydosalicylic Acids. By J. C. Duff and E.J. Bills. Hexamethylenetetramine and salicylic acid, heated in aqueous solution, gave, not the expected 3- and 5-hydroxymethylsalicylic acids, but 3- and 5-aldehydosalicylic acids, which were readily separated by means of benzene. m- and p-hydroxybenzoic acids under the same conditions gave complex amorphous products. Preparation of 3- and 5-Aldehydosalicylic Acid.—salicylic acid (40 g.) hexamethylenetetramine (27 g.), and H2O (300 c.c.) were boiled under reflux for 16 hrs., the cooled solution acidified with 4N-HCl(300 c.c.),and the yellow ppt. dried and extracted with four lots of C6H6 (100 c.c.), at 70°. The insol. Portion, cryst. From boiling h2o (charcoal), yielded 7.5 g. of 5-aldehydosalicylic acid. The c6h6 solution was evaporated, the residue dissolved in 3N-NH3(200 c.c.), and 10% BaCl2 (100 c.c.) and 2N-NaOH (50 c.c.)added at 50°.After 2 hrs., the ppt. of barium 3-aldehydosalicylate was collected and decomposed with dilute HCl, and 3.3 g. of 3-aldehydosalicylic acid obtained by crystallisation of the resulting ppt. from boiling H2O. Salicylic acid (20 g.) was recovered from the alkaline filtrate. The identity of the acid was confirmed by their aldehyde reactions, m.p.’s (also of their oximes), equiv.(titration), and by conversion into the corresponding hydroxyisophthalic acids and hydroxymethylsalicylic acids by oxidation and reduction respectively. The two aldehydosalicylic acids, unlike salicylic acid, when titrated in EtOH with Ba(OH)2 aq., had equiv. 83, exactly half of that found in H2O. The Technical college ,Birmingham. Received. May 3rd, 1932. J. C. Duff & E. J. Bills, JCS 1934, 1305-1308 |
5楼2009-03-31 17:12:11
