反应详情

温度

150 °C

To a 100 ml round-bottomed flask containing potassium hydroxide (4.7 g; 82.0 mmol) dissolved in water (20 ml) was successively added 4-methoxyphenol (10.0 g; 80.6 mmol) and methyl 4-chloro-3,5-dinitrobenzoate (20.2 g; 77.5 mmol). The flask was fitted with a reflux condenser and the reaction heated at 150° C. (oil bath) for 3 hours. After cooling to room temp, the reaction mixture was transferred to a large mortar and triturated with cold 2N NaOH (100 ml) to remove unreacted phenol. The solid was collected by filtration and air-dried to give 21.5 g of crude product. Crystallization from absolute ethanol gave 17.7 g (65.6%) of pure methyl 3,5-dinitro-4-(4-methoxyphenoxy)benzoate as light yellow needles. 300 MHz 1H NMR (CDCl3) d 3.77 (s, 3H, OCH3), 4.02 (s, 3H, OCH3), 6.82 (m, 4H, ArH), 8.70 (s, 2H, ArH).

1. customThe flask was fitted with a reflux condenser
2. temperatureAfter cooling to room temp
3. customtriturated with cold 2N NaOH (100 ml)
4. customto remove unreacted phenol
5. filtrationThe solid was collected by filtration
6. customair-dried
7. customto give 21.5 g of crude product
8. customCrystallization from absolute ethanol