Glycine → Acryloylglycine

Temperature

0 °C

7.5 g (0.1 mol) mol) glycine was dissolved in 100 ml 2 N NaOH. The solution was cooled to 0° C. and 10.8 g (0.12 mol) acryloyl chloride was added dropwise over 45 minutes, while the temperature was kept below 10° C. The reaction was allowed to continue for one hour at 10° C. The reaction mixture was extracted 2 times with 50 ml tert. butyl methyl ether. The pH was adjusted to pH=3, using a concentrated hydrochloric acid solution and the reaction mixture was saturated with sodium chloride. The mixture was extracted 5 times with 100 ml n.-pentanol. The pooled n.-pentanol fractions were dried over Na2SO4 and evaporated under reduced pressure, after addition of a small fraction BHT as stabilizer. 4.2 g (32.5%) of N-acryloyl-glycine was isolated (m.p. 124-126° C.). N-acryloyl-glycine is Comparative Monomer 5 (see below).

1. customwas kept below 10° C
2. extractionThe reaction mixture was extracted 2 times with 50 ml tert. butyl methyl ether
3. extractionThe mixture was extracted 5 times with 100 ml n
4. dry with material-pentanol fractions were dried over Na2SO4
5. customevaporated under reduced pressure
6. additionafter addition of a small fraction BHT as stabilizer

ORD record

ord-944211383c444fa4b64675c3187bedf3

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08978554B2