(4-Nitrophenyl)acetic acid → Actarit

Participants

Reaction Steps

150 g (0.83 mole) of 4-nitrophenylacetic acid are heated to 95° C. in 1.5 liters of glacial acetic acid. With vigorous stirring, 160 g (2.86 moles) of iron powder are added in portions in such a manner that the internal temperature does not rise above 105° C. Towards the end of the reaction, the reaction mixture clears up. 200 ml of acetic anhydride are added, and stirring is afterwards continued for a further 30 minutes at 100° C. Cooling to room temperature is allowed to take place; this is followed by suction filtration from formed iron salts, concentration to half the volume, and dilution with 1.5 liters of water. Extraction is effected three times with, in each case, one liter of ethyl acetate. This is followed by washing the organic phase with water and then concentrating it to dryness to obtain 133 g (83.1% of theory) of 4-acetamidophenylacetic acid (m.p. 168° to 170° C.).

Provenance & Evidence