4-Methoxyphenol → p-(p-Nitrophenoxy)anisole

Participants

Reaction Conditions

Reaction Steps

4-Methoxyphenol (25 g, 0.20 mol) was heated under a nitrogen atmosphere to 70° C. during which time the solid melted. Eighty-five percent potassium hydroxide (12.4 g, 0.19 mol) was added all at once and the mixture stirred at 70° C. for 1 hour. 1-Bromo-4-nitrobenzene (33 g, 0.16 mol) and copper powder (0.1 g, 1.57 mmol) were added and the mixture stirred at 190° C. for 3 hours. After cooling to room temperature, the residue was partitioned between benzene and water. The organic layer was then extracted two times with 5% KOH, dried (MgSO4) and the solvent removed under reduced pressure to give a brown solid. Purification by HPLC (hexane-methylene chloride) gave 4-methoxy-4'-nitrodiphenyl ether as a yellow crystalline solid (19.05 g, 49%), mp 107°-109° C.

Provenance & Evidence