Diethyl Ether → N-Acryloyl-D-glucamine

Participants

Reaction Steps

1-Amino-1-deoxy-D-glucitol (0.16 mol; 29 g) and 0.2 g NaNO2 were dissolved under a nitrogen atmosphere at 0° C. in 100 ml of a 0.3M K2CO3 solution. Acryloyl chloride (0.32 mol; 28.96 g) was added under vigorous stirring. The reaction was carried out similar to the synthesis of 1. After addition of ether, white crystals and a yellow oil were formed. The crystals were separated and gave the product, while the oil was discharged. Stepwise addition of 2 l of ether to the mother liquid and storing it in the refrigerator gave more of the desired product. For further purification the crystals were recrystallized twice from water/ethanol/ether. Yield: 22.2 g (59%), m.p.: 125° C.

Provenance & Evidence