1-Methylimidazole → HCID 178460461, compound

11-Bromoundecanol (10.00 g, 40 mmol) was dissolved in 40 ml of dry tetrahydrofuran (THF) in a two-necked round bottom flask. The flask was cooled in an ice-bath and triethylamine (5.13 mL, 40 mmol) in THF (40 mL) was added to the stirring solution. Acryloyl chloride (3.65 g, 40 mmol) dissolved in 40 ml of THF was added dropwise to the stirring solution over a period of 15 min under N2 atmosphere. The mixture was further stirred for 2 days at room temperature and was filtered. The filtrate was washed with 2% sodium bicarbonate solution to remove any unreacted acid chloride and dried over anhydrous MgSO4. The dried solution was filtered and the filtrate was passed through a short column of neutral alumina, using CH2Cl2 as the light yellow liquid (yield 10.58 g, 87%). Under N2 atmosphere, a mixture of 11-bromoundecylacrylate (6.08 g, 20 mmol) and 1-methylimidazole (1.64 g, 20 mmol) and a small amount of 2,6-di-tert-butyl-4-methylphenol (inhibitor) was stirred at 40° C. for 48 h, and yielded a viscous liquid. The viscous liquid was purified by the precipitation method with diethyl ether to obtain a yellow viscous liquid 1-(11-acryloyloxyundecyl)-3-methylimidazolium bromide. The viscous liquid was dried under vacuum at room temperature to obtain a white waxy solid (5.73 g, 74%).

1. temperatureThe flask was cooled in an ice-bath
2. additionwas added dropwise to the stirring solution over a period of 15 min under N2 atmosphere
3. filtrationwas filtered
4. washThe filtrate was washed with 2% sodium bicarbonate solution
5. customto remove any unreacted acid chloride
6. dry with materialdried over anhydrous MgSO4
7. filtrationThe dried solution was filtered
8. customyielded a viscous liquid
9. customThe viscous liquid was purified by the precipitation method with diethyl ether

ORD record

ord-88935d002b6f4333bcab82092f2ee1c3

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08920682B2