Acetic Acid → Methyl 2-amino-5-chlorobenzoate

Participants

Reaction Steps

1 liter of glacial acetic acid and 10 liters of ice-water are added to a solution of 2.0 kg of methyl 2-aminobenzoate in 15 liters of dichloromethane. 1.9 kg of calcium hypochlorite are added at 10° with vigorous stirring, during which the temperature should not rise above 15°. The mixture is stirred for a further 6 hours and left to stand for 16 hours. The dichloromethane is separated off, the aqueous phase is washed with dichloromethane, and the combined organic phases are washed with a 10% Na2SO3 solution (warming!). The combined dichloromethane phases are stirred with 2 kg of silica gel, 200 g of activated carbon and 2 kg of sodium sulfate. The phases are separated, the dichloromethane is removed, 10 liters of nhexane are added, the mixture is left to stand at 0-5° for 16 hours, and the product is separated off, giving 1.6 kg of methyl 2-amino-5-chlorobenzoate (“1”).

Provenance & Evidence