Chloromethyl Methyl Ether → N-methoxymethyl-N-methylpyrrolidinium chloride

Temperature

5 °C

A 30.0 g quantity of N-methylpyrrolidine (reagent, product of Tokyo Kasei Co., Ltd.) was dissolved in 120 g of methyl acetate, followed by replacement with nitrogen. A 31.2 g quantity of chloromethyl methyl ether (reagent, product of Tokyo Kasei Co., Ltd.) was added dropwise to the solution at 5° C. over a period of 1 hour. The mixture was stirred at 5° C. for 1 hour, the temperature was slowly raised, and the mixture was stirred at room temperature for 10 hours to complete the reaction. The reaction mixture was filtered, and the solid product was washed with 150 g of methyl acetate and 150 g of acetone. The washed product was dried in a vacuum, giving 53.7 g of N-methoxymethyl-N-methylpyrrolidinium chloride. The chloride salt (53.7 g) obtained was dissolved in 125 g of methanol, and 99.6 g of 30% HBF4 methanol solution was added to the solution. Nitrogen was bubbled through the mixture at 130° C. to remove methanol, hydrogen chloride and excessive HBF4 to obtain 70.2 g of the desired electrolyte, i.e., N-methoxymethyl-N-methylpyrrolidinium tetrafluoroborate (water content: 20 ppm). The electrolyte was used to prepare 100 g of an electrolytic solution of the following composition within a glove box having an argon atmosphere with a dew point of −60° C. Calcium oxide (1.0 g) was thereafter added to the solution.

1. temperaturethe temperature was slowly raised
2. stirringthe mixture was stirred at room temperature for 10 hours
3. customthe reaction
4. filtrationThe reaction mixture was filtered
5. washthe solid product was washed with 150 g of methyl acetate and 150 g of acetone
6. customThe washed product was dried in a vacuum

ORD record

ord-5281f15661c447fe813f5bab2dd546b2

Source dataset

uspto-grants-2011_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08029689B2