Ionic Liquid 1-Butyl-3-methylimidazolium Bromide ([Bmim][Br]) Acted as Both Solvent and Catalyst for a Green Reaction of Cross Benzoin Condensation
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Abstract
Cross benzoin condensation using room temperature ionic liquids, namely 1-butyl-3-methylimidazolium bromide ([Bmim][Br]), acted as catalyzed and a solvent under NaOH base condition to afford desired cross-benzoin products 4a-i in satistactory yields (60-70%.) Homo-benzoin condensation 5a-d and 6a also were occurred as side reactions in 9-18% yields.
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References
Breslow, R. (1958). On the mechanism of Thiamine action. IV.1 evidence from studies on model systems. Journal of the American Chemical Society, 80, 3719–3726. DOI: 10.1021/ja01547a064.
Lapworth, A. (1903). Reaction involving the addition of Hydrogen Cyanide to carbon compounds. Journal of the Chemical Society Transactions, 83, 995–1005. DOI: 10.1039/CT9038300995.
Sudhan, S.P.N., Nasir Ahmed, R., Kiyani, H., & Sheik Mansoor, S. (2018). Ionic liquid 1-Butyl-3-methylimidazolium Bromide: A green reaction media for the efficient synthesis of 3-Methyl-1,4-diphenyl-1,4,5,7-tetrahydro-yrazolo[3,4-d]pyrimidine-6-ones/thiones using Phthalimide N-sulfonic acid as catalyst. Journal of Saudi Chemical Society, 22, 269–278. DOI: 10.1016/j.jscs.2016. 07.001.
Noei, J., Khosropour, A.R., & Mirjafari, A. (2012). The combination of 1-Butyl-3-methylimidazolium Bromide and Trichloro (trifluoromethanesulfonato) titanium (IV) as a new protocol for the synthesis of Aryl Nitriles. Bulletin of the Korean Chemical Society, 33(6), 2102–2104. DOI: 10.5012/bkcs.2012.33.6.2102.
Shekouhy, M., Kordnezhadian, R., & Khalafi-Nezhad, A. (2018). Ultrasound-promoted catalyst-free synthesis ofα-Aminonitriles in 1-Butyl-3-methylimidazolium Bromide ([Bmim]Br) as a reusable neutral ionic liquid. Organic Chemistry Research, 4(1), 1–10. DOI: 10.22036/ORG. CHEM. 2017.94388.1099.
Monfared, A., & EsmaeeliA, A. (2016). One-pot condensation for synthesis 2-Methyl-4-phenylpyrano[3, 2- c] chromen-5(4H)-one and synthesis of Warfarin by ionic liquid catalysis. Iranian Journal Pharmaceutical Research, 15(3), 343–367. DOI: 10.22037/IJPR. 2016.1885.
Phungpis, B., & Hahnvajanawong, V. (2020). 1-Butyl-3-methylimidazolium Bromide as a solvent and precatalyst for stetter reaction. Asian Journal of Chemistry, 32(8), 2028–2032. DOI: 10.14233/ajchem.2020.22711.
Hahnvajanawong, V., Waengdongbung, W., Piekkaew, S., Phungpis, B., & Theramongkol, P. (2013). Benzoin condensation of Aromatic Aldehydes catalysed by N,N-Dimethylbenzimidazolium Iodide and NaOH under green conditions. Science Asia, 39, 50–55. DOI: 10.2306/scienceasia1513-1874.2013.39.050.
Hahnvajanawong, V., Phungpis, B., & Theramongkol, P. (2009). Stetter reaction catalysed by N,NDimethyl benzimidazolium Iodide and Sodium hydroxide in ionic liquid. ACGC Chemical Research Communications, 23, 26–30.
Phungpis, B., Hahnvajanawong, V., & Theramongkol, P. (2014). Benzoin condensation and stetter reactioncatalysed by N,N-Dimethylbenzimidazolium Iodide in [Bmim] [OH]. Oriental Journal of Chemistry, 30, 933–939. DOI: 10.13005/ojc/300303.
Breslow, R. (1958). On the mechanism of Thiamine action. IV. Evidence from studies on model systems. Journal of the American Chemical Society, 80, 3719–3726. DOI: 10.1021/ja01547a064.
Buckingham, J., Cadogan, D. G., Raphael, R. A., Rees, C. W., & an International Advisory Board. (1982). Dictionary of organic compounds. 5th Edition. New York: Chapman and Hall.
Stetter, H., & Kuhlmann, H. (1991). Catalyzed nucleophilic addition of Aldehydes to electrophilic double bonds. Organic Reacions, 40, 407–496. DOI: 10.1002/0471264180.or040.04.