4-Methoxyphenol → Methyl 3,5-dinitro-4-(4-methoxyphenoxy)-benzoate

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence