反应详情

Diethyl oxalate (30 mL) in 20 mL of dry ether was added with stirring to 19 g of potassium ethoxide suspended in 50 mL of dry ether. The mixture was cooled in an ice bath and 20 mL of 3-nitro-o-xylene in 20 mL of dry ether was slowly added. The thick dark red mixture was heated to reflux for 0.5 hr, concentrated to a dark red solid, and treated with 10% sodium hydroxide until almost all of the solid dissolved. The dark red mixture was treated with 30% hydrogen peroxide until the red color changed to yellow. The mixture was treated alternately with 10% sodium hydroxide and 30% hydrogen peroxide until the dark red color was no longer present. The solid was filtered off and the filtrate acidified with 6 N hydrochloric acid. The resulting precipitate was collected by vacuum filtration, washed with water, and dried under vacuum to give 9.8 g (45% yield) of 2-methyl-6-nitrophenylacetic acid as an off-white solid. The solid was hydrogenated in methanol over 10% palladium on carbon to give 9.04 g of the title compound as a white solid.

1. temperatureThe mixture was cooled in an ice bath
2. temperatureThe thick dark red mixture was heated
3. temperatureto reflux for 0.5 hr
4. concentrationconcentrated to a dark red solid
5. additiontreated with 10% sodium hydroxide until almost all of the solid
6. dissolutiondissolved
7. additionThe dark red mixture was treated with 30% hydrogen peroxide until the red color
8. additionThe mixture was treated alternately with 10% sodium hydroxide and 30% hydrogen peroxide until the dark red color
9. filtrationThe solid was filtered off
10. filtrationThe resulting precipitate was collected by vacuum filtration
11. washwashed with water
12. customdried under vacuum