4- Nitro-o-xylene

Dinitro-l, 2-dime tbylbenzene, ndls (from ale), mp 56—60° 89—90° obtd with other products on nitrating o-xylene or 3-nitro-o-xylene with coned nitric acid (Ref 1, p369 Ref 2, pl8l)... 

Carboxy-U-nitrotoluene, AM35 5-Carboxy-2-nitrotoluene, AM3 L-Carboxy-3-nitro-o-xylene, AP10... 

Nitro-o-xylene, AN11 l+-Nitro-o-xylene, ANl -2-Nitro-m-xylene, AN13... 

The following mononitro derivatives are known 4-nitro- and 3-nitro-o-xylene and 2-nitro-p-xylene ... 

A solution of n-butyl nitrite (2.6 mol) and 3-nitro-o-xylene (2.0 mol) dissolved in 750 ml of dimethylformamide were cooled to -60°C and potassium t-butoxide (4.56 mol) dissolved in 750 ml of dimethylform-amide added over 3 hours. Thereafter, 300 ml water were added followed by 300 ml HOAc until a pH 5-6 reached. The mixture was then poured into 6 kg of ice water, the residue filtered, washed with water, and dried. The precipitate was placed in a suspension of about 3L of toluene at 80-90 °C 2 hours, the mixture filtered, dried, and the product isolated in 77% yield, 98% purity, mp = 190-192°C. 

Starting with 3-nitro-o-xylene (28), 3-(2-methyl-6-nitrophenyl)-4,5-dihydro-isoxazole (31) is synthesized via the benzaldehyde oxime 29. Subsequent reduction of the nitro group, replacement of the corresponding amino group by methyl... 

Blanksma, Chem. Zentr, 1909, II, 1219. 4 5-Dibromo-3-nitro-o-xylene... 

---