A
500-ml. three-necked flask is fitted with a stirrer, a
dropping funnel, and a
thermometer placed so that the bulb is near the bottom of the flask. In the flask are placed
89 g. (1 mole) of 2-nitropropane (Note
1),
50 ml. of dioxane, and
10 ml. of a 40% aqueous solution of benzyltrimethylammonium hydroxide (Triton B) (Note
2), and the contents of the flask are warmed to 70°.
Eighty-six grams (1 mole) of redistilled methyl acrylate (Note
3) is added, with stirring, during 15 minutes. The temperature rises to about 100° during the addition and then drops to about 85°. The mixture is stirred and heated on a
steam bath for 4 hours. After cooling, the contents of the flask are acidified with dilute
hydrochloric acid and extracted with
ether. The
ether layer is washed twice with water, then with approximately
50 ml. of 0.1% sodium bicarbonate solution, and finally again with water. After the ethereal solution has been dried over anhydrous
sodium sulfate, the drying agent is separated, the solvent is removed by distillation, and the product is distilled through a short
fractionating column. A nearly colorless oil is obtained in a yield of
140–151 g. (
80–86%); b.p.
79°/1 mm.;
nD20 1.4408.