تفاعل #77951

معادلة التفاعل

water

n-butyl nitrite

3-nitro-o-xylene

potassium tert-butoxide

→

2-methyl-6-nitrobenzaldoxime

المذيبات

acetic acid

dimethylformamide

dimethylformamide

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONDuring the addition
2. 2
   أخرىrises to −10° C.
3. 3
   أخرىa yellow suspension is formed
4. 4
   أخرىthe residue that has formed
5. 5
   ترشيحis filtered off with suction
6. 6
   غسيلwashed with 5 l of water
7. 7
   أخرىdried in a drying cabinet at 30° C. overnight
8. 8
   أخرىat 80-90° C.
9. 9
   أخرىfor 2 hours
10. 10
    درجة الحرارةAfter cooling
11. 11
    ترشيحthe product is filtered off with suction
12. 12
    أخرىdried

الإجراء التجريبي

A solution of 274 g (2.6 mol) of n-butyl nitrite (97% pure) and 300 g (2.0 mol) of 3-nitro-o-xylene (97% pure) in 750 ml of dimethylformamide is cooled to from −55 to −60° C., and a solution of 522 g (4.56 mol) of potassium tert-butoxide in 750 ml of dimethylformamide is added dropwise at this temperature, over a period of 2.5 hours. The color of the solution changes from yellow to deep red, and the consistency becomes viscous. The reaction is monitored by HPLC. For work-up, initially 300 ml of water are added, and subsequently approximately 300 ml of glacial acetic acid, until the pH is 5-6. During the addition, the temperature rises to −10° C., and a yellow suspension is formed. The reaction mixture is subsequently poured into 6 kg of ice-water, and the residue that has formed is filtered off with suction, washed with 5 l of water and dried in a drying cabinet at 30° C. overnight. This gives 339 g of a light-beige crude product which is freed from impurities by suspending it in approximately 3 l of toluene at 80-90° C. for 2 hours. After cooling, the product is filtered off with suction and dried. This gives 276 g of 2-nitro-6-methylbenzaldoxime.

المصدر