ChemicalBook CAS DataBase List N-BUTYL METHANESULPHONATE

N-BUTYL METHANESULPHONATE synthesis

5synthesis methods

Product Name:N-BUTYL METHANESULPHONATE
CAS Number:1912-32-9
Molecular formula:C5H12O3S
Molecular Weight:152.21

124-63-0

71-36-3

1912-32-9

To an anhydrous dichloromethane (10 mL) solution of n-butanol (500 mg, 6.7 mmol) was added sequentially pyridine (0.82 mL, 10.1 mmol) and methanesulfonyl chloride (0.78 mL, 10.1 mmol). The reaction mixture was stirred at 0 °C and gradually warmed to room temperature. After 6 hours of reaction, the reaction was quenched with methanol and the reaction solution was subsequently concentrated. The concentrate was diluted with ethyl acetate (50 mL) and washed sequentially with 1 M hydrochloric acid (10 mL), saturated sodium bicarbonate solution (10 mL) and saturated saline (10 mL). The organic layer was dried with anhydrous sodium sulfate, filtered and concentrated. The resulting residue was purified by silica gel column chromatography to afford n-butyl methanesulfonate (compound 2) as a colorless oil (0.94 g, 92% yield).1H NMR (400 MHz, CDCl3) δ 4.24 (t, J = 13.2, 6.4 Hz, 2H), 3.01 (s, 3H), 1.76-1.72 (m, 2H), 1.48- 1.42 (m, 2H), 0.96 (t, J = 12.8, 7.6 Hz, 3H); 13C NMR (100 MHz, CDCl3) δ 69.99, 37.30, 31.05, 18.67, 13.48. High-resolution mass spectrometry (ESI) calculated value [C5H12SO3 + Na]+ 175.0405, measured value 175.0401.

124-63-0
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$10.00/5g

71-36-3 Synthesis

71-36-3
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$14.00/25mL

1912-32-9
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$6.00/1g

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]

1927-68-0 Synthesis