Hydroquinone → HCID 178460460, compound

(From Yu et al., Macromolecules 2008, 41, 3389-3392.) 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. 2-methyl acryloyl chloride (4.08 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-bromoundecyl methylacrylate (6.08 g, 20 mmol) and 1-methylimidazole (1.64 g, 20 mmol) and a small amount of 1,4-dihydroxybenzene (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 yellow viscous liquid 1-(2-acryloyloxyundecyl)-3-methylimidazolium bromide. The viscous liquid was dried under vacuum at room temperature as the 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-a7889891f95f41c8abd7756242ecc8a4

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08920682B2