反应详情

温度

23 °C

A solution of 8.2 g (50 mmole) of 4-tertbutylanisole in 15 ml of ethylene dichloride was placed in a 40 ml two necked round-bottomed flask equipped with a thermometer, a dropping funnel and magnetic stirring bar. The flask was placed in an ice-water bath and the contents were stirred and cooled. When the temperature reached +4° C., 4.72 g (3.32 ml, 52.4 mmol) of 70% nitric acid was added at such a rate that the temperature of the reaction mixture remained below 10° C. The completion of the acid addition took 15 minutes. Then the reaction mixture was stirred for 15 minutes while the flask was still immersed in the ice-water bath. After this time the reaction mixture was allowed to warm-up to 23° C. and left for 3 more hours with stirring to complete the nitration. The stirring was then stopped and the lower (organic) layer was collected. From this solution ethylene dichloride is removed by rotary evaporation at 40° C. under 20 mmHg and an oily residue was subjected to vacuum distillation. A 6" Vigreux column and a pressure of 1 mmHg was applied. These conditions afforded separation of the 4-nitroanisole bp 86° C. from 2-nitro-4-tertbutylanisole bp 102°-105° C. It resulted in the collection of 7.576 g of 99.1% pure 2-nitro-4-tertbutylanisole and 2.116 g of 96.4% pure 4-nitroanisole, mp 54° C. wth a total yield of 72.5% of 2-nitro-4-tertbutylanisole.

1. customequipped with a thermometer, a dropping funnel and magnetic stirring bar
2. customThe flask was placed in an ice-water bath
3. temperaturecooled
4. customreached +4° C.
5. customremained below 10° C
6. additionThe completion of the acid addition
7. stirringThen the reaction mixture was stirred for 15 minutes while the flask
8. waitleft for 3 more hours
9. stirringwith stirring
10. customthe lower (organic) layer was collected
11. customFrom this solution ethylene dichloride is removed by rotary evaporation at 40° C. under 20 mmHg
12. distillationan oily residue was subjected to vacuum distillation
13. customThese conditions afforded
14. customseparation of the 4-nitroanisole bp 86° C. from 2-nitro-4-tertbutylanisole bp 102°-105° C