N-BUTYL METHANESULPHONATE synthesis
- Product Name:N-BUTYL METHANESULPHONATE
- CAS Number:1912-32-9
- Molecular formula:C5H12O3S
- Molecular Weight:152.21
Yield:1912-32-9 100%
Reaction Conditions:
with triethylamine in dichloromethane at 0; for 1 h;
Steps:
1-Butyl-3-methylimidazolium methanesulfonate (IV)
First step, a stirred solution of n-butanol (4.05 g, 49.3 mmol) in dried dichloromethane (20.0 mL) was cooled to 0 °C and then methanesulfonyl chloride (4.58 mL, 59.2 mmol) was added slowly at 0 °C, followed by triethyl amine (8.26 mL, 59.2 mmol). The stirring was continued at 0 °C for 1 h. After the completed conversion, the reaction mixture was filtered and evaporated to obtain the n-butyl methanesulfonate in quantitative yield. Second step, to a solution of 1-methylimidazole (6.47 g, 78.8 mmol) in acetonitrile (50.0 mL) was added n-butyl methanesulfonate (10.00 g, 65.7 mmol) at room temperature. Then, the reaction temperature was reached to 60 °C with stirring and stirred for 24 h. After the completed conversion, acetonitrile was removed by rotary evaporator. The reaction mixture was extracted with EtOAc (3 20 mL) to remove neutral organic compounds. Then, the ionic liquid layer was concentrated in vacuum to obtain the [bmim][OMs] (IV) in 92% yield (8.11 g) as a yellow oil; CAS No. 342789-81-5; 1H NMR (400 MHz, CDCl3): δ 9.87 (s, 1H), 7.39 (brs, 1H), 7.29 (brs, 1H), 4.24 (t, 2H, J = 7.6 Hz), 4.02 (s, 3H), 2.76 (s, 3H), 1.85 (quint, 2H, J = 7.2 Hz), 1.35 (sext, 2H, J = 7.6 Hz), 0.94 (brt, 3H, J = 7.2 Hz); 13C NMR (100 MHz, CDCl3): δ 137.43, 123.61, 121.85, 49.45, 39.45, 31.91, 19.25, 13.25, 8.53.
References:
Ketsomboon, Nutthanicha;Saeeng, Rungnapha;Srisook, Klaokwan;Sirion, Uthaiwan [Tetrahedron Letters,2021,vol. 80,art. no. 153325]
51761-36-5
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