溴化氢的冰乙酸溶液脱除苯磺酰基的研究  

Investigation of Cleavage of Benzenesulfonyl by Hydrogen Bromide in Acetic Acid

作　　者：黄志平[1] 张鸣[1] 项丰顺[1] 周黎明[1] 

机构地区：[1]防化指挥工程学院三系,北京102205

出　　处：《广东化工》2009年第5期29-30,95,共3页Guangdong Chemical Industry

摘　　要：采用溴化氢的冰乙酸溶液与苯酚的混合物快速脱除N–苯磺酰基–4–乙酰基哌啶–4–羧酸乙酯中的苯磺酰基,避免了酸解法脱除苯磺酰基引起反应物的脱羧反应,得到了目标产物4–乙酰基哌啶–4–羧酸乙酯,产率和纯度高。通过对脱除反应液的分析,表明溴化氢的冰乙酸溶液与苯酚的混合物对苯磺酰基的脱除可能是一个氧化-还原过程,苯酚在其中起了消除溴并防止脱除产物溴化的作用。Hydrogen bromide in acetic acid in presence of phenol was employed as a reagent for the rapid cleavage of benzenesulfonyl group from ethyl -4-carboxylate. Decarboxylation of the reactant, which occurred when acidic hydrolysis was used as a method for the cleavage of benzenesulfonyl group, was avoided. The target product obtained was in high yield and purity. It was deduced that the cleavage mechanism may be an oxidation-reduction process involving the benzenesulfonyl group and hydrogen bromide by analyzing compounds in cleavage solution. Bromination of cleavage product was prevented by removing bromine with phenol.

关 键 词：溴化氢 苯酚 苯磺酰基 氧化-还原过程 

分 类 号：TQ453.22[化学工程—农药化工] O636.1[理学—高分子化学]