Anisole → (4-Methoxyphenyl)(3-nitrophenyl)methanone

Participants

Reaction Conditions

Reaction Steps

To a cold (0° C.) mixture of anisole (17.7 mL, 0.162 mol, 1.0 eq.) and aluminium trichloride (26.9 g, 0.202 mol, 1.25 eq.) in 1,2-dichloroethane (140 mL) was slowly added 3-nitrobenzoylchloride (30 g, 0.162 mol). The cooling bath was removed, and the reaction mixture was stirred 2 h at 20° C. The reaction mixture was poured into ice water. Concentrated hydrochloric acid (5 mL) was added. The aqueous layer was extracted with dichloromethane (2 times). The combined organic layers were dried over sodium sulfate, filtered and the volatiles were removed in vacuo. Purification by flash chromatography afforded the title compound (35.1 g, 84%) as an orange solid, m.p.: 88-89° C.

Provenance & Evidence