2-Chloro-4-methyl-1-nitrobenzene

clear yellow liquid after melting

Silak reaction tube equipped with a magnetic stirrer was charged with 6.2 mg of silver sulfate, 36.3 mg of copper acetate, 12.5 mg of 2, 9-dimethyl-1, 10-o-phenanthroline, 36.2 mg of 2-nitro-5-methylbenzoic acid and 17.5 mg of sodium chloride4 mL of dimethyl sulfoxide. The reaction was heated at 160 ° C for 24 hours in the presence of oxygen. After the reaction was completed, distilled water was added to quench the reaction, extraction was performed three times with ethyl acetate, 10 mL each, and the combined organic phases were concentrated, 14.8 mg of 2-nitro-5-methylchlorobenzene was obtained in a yield of 43percent.Concentrated nitric acid (16 mL) was slowly added, at 0° C., to a solution of 3-chlorotoluene (3 mL, 25.4 mmol) and concentrated sulfuric acid (6 mL) in glacial acetic acid (20 mL) and the resulting mixture was stirred for 24 hours allowing the temperature to rise until room temperature. The reaction mixture was then poured into ice-water and partitioned between water and diethyl ether. The aqueous phase was separated and extracted twice with diethyl ether ; the combined organic extracts were washed with water and brine, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The yellow oily residue was purified on a silica gel plug and twice by flash chromatography to give 1.22 g (14percent yield) of 2-chloro-4-methyl-1-nitro-benzene as a yellow oil and 3.39 g (39percent yield) of 4-chloro-2-methyl-1-nitro-benzene.2-Chloro-4-methyl-1-nitro-benzene (1.2 g, 6.99 mmol) in a mixture of water and pyridine (2/1, 30 mL) was heated at 90 C. then potassium permanganate (5.2 g, 32.9 mmol) was added in 4 portions at intervals of 1.5 hours. The reaction mixture was heated at 90 C. for 8 hours and then more potassium permanganate (2 g) was added and the resulting mixture was stirred at 90 C. overnight. More potassium permanganate (2 g) was added and the resulting mixture was stirred at 90 C. for 1 hour, the solid was filtered off on a CELITE pad. Water (50 mL) was added to the filtrate; the resulting mixture was acidified until pH<2 and was extracted 3 times with ethyl acetate. The combined organic extracts were washed with water and brine, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to give 1.19 g (84% yield) of 3-chloro-4-nitro-benzoic acid as a light yellow solid without further purifications

Molecular Weight:171.58
XLogP3:2.7
Hydrogen Bond Acceptor Count:2
Exact Mass:171.0087061
Monoisotopic Mass:171.0087061
Topological Polar Surface Area:45.8
Heavy Atom Count:11
Complexity:157
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes