Reactions between hexamethylenetetramine and phenolic compounds Part I A new method for the preparation of 3-and 5-aldehydosalicylic acids
Reactions between hexamethylenetetramine and phenolic compounds Part I A new method for the preparation of 3-and 5-aldehydosalicylic acids
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DOI：
10.1039/jr9320001987
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发表时间：
1932-01-01
期刊：
影响因子：
--
通讯作者：
Bills, EJ
中科院分区：
文献类型：
--
作者：
Duff, JC;Bills, EJ
3-和5-醛水杨酸的制备。-水杨酸（40 g）、六亚甲基四胺（27 g）和氢氧根（300 cc）回流煮沸16小时。用4N-HCl （300cc）酸化的冷却溶液，黄色ppt。用四批C6H6（100毫升）在70英寸的温度下干燥和提取。insol。部分结晶。从沸水H， O（木炭）中，得到7.5克5-醛水杨酸。蒸发C6H溶液，将残留物溶解在3N-NH （200cc）和10% BaCl （100cc）和2N-NaOH （50cc）中，温度为60℃。2小时后。， ppt。收集3-醛水杨酸钡，用稀HC1分解，所得ppt结晶得到3.3 g的3-醛水杨酸。从碱性滤液中回收水杨酸（20 g）。通过它们的醛反应、m. p. s（也包括它们的肟）、滴定、氧化和还原分别转化为相应的羟基间苯二甲酸和羟甲基水杨酸，确定了这些酸的身份。
Preparation of 3-and 5-Aldehydosalicylic Acids.-Salicylic acid (40 g.) hexamethylenetetramine (27 g.), and H, O (300 cc) were boiled under reflux for 16 hrs., the cooled solution acidified with 4N-HCl (300 cc), and the yellow ppt. dried and extracted with four lots of C6H6 (100 cc) at 70”. The insol. portion, cryst. from boiling H, O (charcoal), yielded 7.5 g. of 5-aldehydosalicylic acid. The C6H, solution was evaporated, the residue dissolved in 3N-NH,(200 cc), and 10% BaCl,(100 cc) and 2N-NaOH (50 cc) added at 60”. After 2 hrs., the ppt. of barium 3-aldehydosalicylate was collected and decomposed with dilute HC1, and 3.3 g. of 3-aldehydosalicylic acid obtained by crystallisation of the resulting ppt. from boiling H, O. Salicylic acid (20 g.) was recovered from the alkaline filtrate. The identity of the acids was conhed 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.