Methanol → Methyl 4-chloro-3-nitrobenzoate

To a solution of 10.0 g (49.6 mmol) of 4-chloro-3-nitrobenzoic acid in 100 ml of methanol was added dropwise 11.8 g (99.2 mmol) of thionyl chloride at 0° C. The reaction mixture was refluxed for 2 hours and the solvent was then distilled off under reduced pressure. Ice water was added to the resulting residue. The mixture was made basic by the addition of concentrated ammonium hydroxide. The mixture was extracted three times with ethyl acetate. The combined extracts were washed with water and dried over anhydrous magnesium sulfate. The solvent was then distilled off under reduced pressure to give 10.9 g (>99%) of the desired methyl 4-chloro-3-nitro-benzoate.

1. temperatureThe reaction mixture was refluxed for 2 hours
2. distillationthe solvent was then distilled off under reduced pressure
3. additionIce water was added to the resulting residue
4. additionThe mixture was made basic by the addition of concentrated ammonium hydroxide
5. extractionThe mixture was extracted three times with ethyl acetate
6. washThe combined extracts were washed with water
7. dry with materialdried over anhydrous magnesium sulfate
8. distillationThe solvent was then distilled off under reduced pressure

ORD record

ord-71faab1d520f40acbb1db11654231355

Source dataset

uspto-grants-2001_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06248772B1