2-Chloro-6-nitrobenzoic acid

The organic phase from was heated to 100° C., and 1, 2-dichlorobenzene was distilled off at 15 mbar over 2 hours to a residual content of 4percent by weight.400 mol percent (based on 2-chloro-6-nitrotoluene used) of 65percent strength by weight nitric acid were initially introduced into an autoclave and heated to 140° C. The benzyl alcohol, largely freed from the solvent, was metered in uniformly over the course of 8.5 hours. During this operation, the pressure in the autoclave was kept constant at 10 bar. Escaping nitric acid and 1, 2-dichlorobenzene was not replaced. After the total amount of benzyl alcohol had been pumped in, the mixture was after-stirred for 10 minutes, cooled to 100° C. and decompressed.Aqueous nitric acid was distilled off with a gentle vacuum, and the residue which remained was dissolved with 400 g of 1, 2-dichlorobenzene.Analysis of the mixture revealed 1.44 mol percent of unreacted 2-chloro-6-nitrobenzyl alcohol, 0.26 mol percent of 2-chloro-6-nitrobenzaldehyde and 90 mol percent of 2-chloro-6-nitrobenzoic acid.The mixture was cooled to 25° C. over the course of 4 hours. The precipitated 2-chloro-6-nitrobenzoic acid was filtered off and washed with a small amount of cold 1, 2-dichlorobenzene. Drying gave pure 2-chloro-6-nitrobenzoic acid in 78percent yield (based on 2-chloro-6-nitrotoluene used).The organic phase from was heated to 140° C. and, over the course of 4 hours, 220 mol percent (based on 2-chloro-6-nitrotoluene used) of 65percent strength by weight nitric acid were added, and the mixture was after-stirred for 2 hours. During this operation, an approximately 9percent strength by weight aqueous nitric acid distilled off, and nitrous gases escaped. Codistilled 1, 2-dichlorobenzene was returned to the batch.Residual nitric acid/water mixture was distilled off and the reaction mixture was cooled to 0° C. over the course of 4 hours. The precipitated 2-chloro-6-nitrobenzoic acid was filtered over and washed with a small amount of cold 1, 2-dichlorobenzene.Drying gave pure 2-chloro-6-nitrobenzoic acid in 60percent yield (based on 2-chloro-6-nitrotoluene).

Molecular Weight:201.56
XLogP3:1.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:200.9828853
Monoisotopic Mass:200.9828853
Topological Polar Surface Area:83.1
Heavy Atom Count:13
Complexity:227
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes