Elbs氧化反应

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利用过硫酸钾在碱性条件下氧化苯酚，然后水解，在苯酚对位引入酚羟基的反应。此反应也被称为 Elbs过硫酸盐氧化反应，此反应与Boyland–Sims氧化类似只是底物由苯胺变为苯酚，机理也与其类似。



反应机理

对位反应位点的特点是由于苯酚的互变异构体决定的，过硫酸盐的氧原子对苯酚进行亲电取代，水解得到产物。




反应实例


【Journal of Medicinal Chemistry, 2007, 50, 350-355】



【Bioorganic and Medicinal Chemistry, 2009, 17, 3414-3425】




【European Journal of Medicinal Chemistry, 2012, 58, 72-83】



【Macromolecules, 2013, 46, 5520-5530】



2,5-Dihydroxypyridine   To 1 (38.0 g, 0.4 mol) and NaOH (80.0 g, 2 mol) in water (1.5 L) at 0℃ was added FeSO4 (2.0 g) in water (20 mL) and K2S2O8 (135.0 g, 0.5 mol). After 20 h at 20 ℃ and filtration, conc H2SO4 was added (cooling) to pH 0.75 and the mixture was heated to 100 ℃ under N2 for 30 min. Cooling, neutralization by 10 N NaOH to pH 6.5, extraction (Soxhlet) with IPA and evaporation afforded 19 g of 2 (42%).

【Behrman EJ, J Am Chem Soc., 1958, 80, 3717】




相关文献

1. Elbs, K. J. Prakt. Chem. 1893, 48, 179-185.

2. Watson, K. G.; Serban, A. Aust. J. Chem. 1995, 48, 1503-1509.

3. Neumann MS， J Org Chem., 1980, 45, 4275

4. Wallace TW， Synthesis, 1983, 1003

5. Behrman EJ， Beil J Org Chem., 2006, 2, 22

6. Dai, K.; Wen, Q.; Liu, X.; Chen, S. Faming Zhuanli Shenqing CN102408401 (2012).


参考文献

一、J.J. Li, Name Reactions: A Collection of Detailed Mechanisms and Synthetic Applications, Elbs oxidation，page 76.

二、reactionflash：Elbs oxidation



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