Methyl Acrylate → Butyl Acrylate

Temperature

80 °C

To a 30 mL pyrex tube were added methyl acrylate (5 mL, 4.78 g, 55.5 mmole), allyl 2-methyl-2-bromopropionate(0.354 mL, 460 mg, 2.2 mmole), copper (I) bromide (318 mg, 2.22 mmole), 2,21-bipyridyl (1.04 g, 6.66 mmole), ethyl acetate (4 mL) and acetonitrile (1 mL). The mixture was degassed by three freeze-pump-thaw cycles and then sealed. The mixture was heated to 80° C. for 3 hours and then after cooling to ambient temperature, the mixture was diluted with ethyl acetate (20 mL). An insoluble precipitate was filtered off and the filtrate was washed twice with dil. HCl and once with NaCl solution. The organic layer was dried over Na2SO4 and concentrated under reduced pressure to yield a poly(butyl acrylate) having an alkenyl group at one end and a bromine atom at the other end (3.93 g, 75%). The molecular weight and the molecular weight distribution of the polymer were found to be 2700 and 1.48, respectively, by GPC analysis (based on polystyrene standard). The number of alkenyl groups introduced into the polymer was 0.81 based on 1H NMR analysis.

1. customThe mixture was degassed by three freeze-pump-thaw cycles
2. customsealed
3. temperatureafter cooling to ambient temperature
4. additionthe mixture was diluted with ethyl acetate (20 mL)
5. filtrationAn insoluble precipitate was filtered off
6. washthe filtrate was washed twice with dil. HCl and once with NaCl solution
7. dry with materialThe organic layer was dried over Na2SO4
8. concentrationconcentrated under reduced pressure

ORD record

ord-248401eb3bc14ac6a3f788af668308b4

Source dataset

uspto-grants-2003_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06667369B2