反应详情

A solution of 2-methoxylaniline (24.6 g, 0.200 mol) in hydrochloric acid (20% aqueous solution, 80 mL) was slowly added to a solution of sodium nitrite (15 g, 0.22 mol) in water (40 mL) at 0 to 5° C. After stirring for 10 minutes, a cooled (0° C.) solution of acrolein (30 g, 0.56 mol) in acetone (200 mL) containing calcium oxide (4.0 g, 72 mmol) was slowly added, followed by a solution of cuprous chloride (2.0 g, 20 mmol) in acetone (20 mL) containing hydrochloric acid (20% aqueous solution, 4 mL). The mixture was stirred at 0 to 30° C. for 3 hours, and then extracted with three 150 mL portions of dichloromethane. The combined organic layers were washed with a saturated aqueous solution of sodium bicarbonate, a saturated aqueous solution of sodium chloride, dried over sodium sulfate, filtered, and concentrated to give a black viscous oil. The crude product was passed through a short silica column to give 10 g of crude product, which was used directly in the next procedure.

1. additionwas slowly added
2. stirringThe mixture was stirred at 0 to 30° C. for 3 hours
3. extractionextracted with three 150 mL portions of dichloromethane
4. washThe combined organic layers were washed with a saturated aqueous solution of sodium bicarbonate
5. dry with materiala saturated aqueous solution of sodium chloride, dried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated
8. customto give a black viscous oil