Water → 1-[2-Methoxy-4-(2-nitro-vinyl)-phenoxymethyl]-naphthalene

Participants

Reaction Steps

36 g of 3-methoxy-4-(naphthalen-1-ylmethoxy)-benzaldehyde, 8.7 9 of ammonium acetate and 10 ml of nitromethane are together heated at reflux for 5 hours in 140 ml of glacial acetic acid. After cooling, the reaction mixture is introduced into 1.5 liters of water. Extraction is carried out twice using 1 liter of ethyl acetate each time. The organic phases are washed 4 once with 500 ml of water and three times using 400 ml of 2N potassium hydrogen carbonate solution each time, dried over magnesium sulfate and concentrated, yielding 1-[2-methoxy-4-(2-nitro-vinyl)-phenoxymethyl]-naphthalene, which can be purified by chromatography on silica gel with ethyl acetate/n-hexane 1:4 and recrystallisation in ethyl acetate/n-hexane, m.p. 120-123° C.

Provenance & Evidence