Nitrobenzene → 4-(4'-Methoxy-biphenyl-4-yl)-4-oxo-butyric acid

Participants

Reaction Steps

A 50 g. portion of p-methoxybiphenyl and 30 g. of succinic anhydride are mixed in 600 ml. of nitrobenzene and cooled to about 5° C. A 73 g. portion of aluminum chloride is added in portions keeping the temperature at about 5° C. The mixture is then stirred for 15 hours and allowed to stand at room temperature. The mixture is poured into ice and then steam distilled until no more nitrobenzene comes over. The residue solidifies and is dissolved in 1,250 ml. of water containing 63 g. sodium carbonate. The solution is boiled with charcoal, filtered and the filtrate is chilled. The precipitate is filtered at room temperature and the gummy mixture is acidified with HCl and cooled. The precipitate is triturated with 50% acetic acid and the insoluble portion is recovered by filtration giving 4'-methoxy-γ-oxo-4-biphenyl-butyric acid.

Provenance & Evidence