Hydrochloric Acid → N-Methacryloyl glycine

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Reaction Steps

Glycine (75 g, 1 mol) is dissolved in 500 ml of 40 g (1 mol) of sodium hydroxide in the ice bath and the clear solution is reacted with 105 g (1 mol) of methacryloyl chloride and 40 g (1 mol) of sodium hydroxide in 150 ml of water simultaneously. The reaction temperature is kept below 5° C. throughout the addition. The reaction mixture is allowed to rise to room temperature and stirred at that temperature for three hours. The clear solution was titrated with 1N HCl to pH 3.0 and extracted with ethylacetate. The combined organic layer is dried over anhydrous magnesium sulfate and evaporated to leave 70 g (46%) of a crystalline material. Melting point 104° C. (literature 104°-105.5° C.). NMR (D2O), 5.7 gamma (s, 1H, =CH2), 5.4 gamma (s, 1H, =CH2), 4.0 gamma (s, 2H, CH2 ), 1.9 gamma (s, 3H, CH3). Purity by neutralization, 100.1%; purity by bromination, 100.8%.

Provenance & Evidence