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Citation: Yang Li, Yuxuan Zhang, Yuhai Tang, Lijuan Wang. Iodide anion-catalyzed green synthesis of m-cresol[J]. University Chemistry, ;2026, 41(7): 326-333. doi: 10.12461/PKU.DXHX202506054 shu

Iodide anion-catalyzed green synthesis of m-cresol

School of Chemistry, Xi'an Jiaotong University, Xi'an 710049, Shaanxi Province, China

Corresponding author: Yang Li, yanglee@mail.xjtu.edu.cn
Received Date: 13 June 2025
Revised Date: 8 September 2025

Phenol and its derivatives are important intermediates in organic synthesis. This experiment combines the iodine anion catalyzed dehydroaromatization and the synthesis of m-cresol, aiming to develop it as a potential undergraduate organic chemistry experiment. This experiment used inexpensive and readily available 3-methyl-2-cyclohexen-1-one as the starting material, tetra-n-butylammonium iodide (n-Bu₄NI) as catalyst, and 1,2-dichloroethane as solvent to achieve the green synthesis of m-cresol. Subsequently, the product was purified via back extraction, followed by structure characterization and purity analysis. In short, the experiment is reasonable, reliable and straightforward, which includes the basic techniques such as inert gas protection, reflux, extraction, back extraction, filtration and distillation, as well as the organic compound characterization, making it highly suitable for undergraduate comprehensive experiments.
- Iodide anion,
- Aromatization,
- Phenol,
- Green synthesis
1. [1]
  J.H.P. Tyman, Synthetic and Natural Phenols, Elsevier: New York, NY, USA, 1996.
2. [2]
  Z. Rappoport, The Chemistry of Phenols, Wiley-VCH: New York, NY, USA, 2003.
3. [3]
  Z. Qiu, C.-J. Li, Chem. Rev. 2020, 120, 10454.
4. [4]
  K.A. Scott, P.B. Cox, J.T. Njardarson, J. Med. Chem. 2022, 65, 7044.
5. [5]
  G.A. Olah, Acc. Chem. Res. 1971, 4, 240.
6. [6]
7. [7]
  X. Liu, J. Chen, T. Ma, Org. Biomol. Chem. 2018,16, 8662.
8. [8]
  Y. Izawa, D. Pun, S.S. Stahl, Science 2011, 333, 209.
9. [9]
  Y.-F. Liang, S. Song, L. Ai, X. Li, N. Jiao, Green Chem. 2016, 18, 6462.
10. [10]
  M.L. Ho, A.B. Flynn, W.W. Ogilvie, J. Org. Chem. 2007, 72, 977.
11. [11]
  S.W. Englund, R.S. Aries, D.F. Othmer, Ind. Eng. Chem. 1953, 45, 189.
12. [12]
  D.F. Othmer, Ind. Eng. Chem. 1953, 45, 193.
13. [13]
14. [14]
15. [15]
16. [16]
17. [17]
1. [1]
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2. [2]
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