Water → 2-Methyl-6-nitrobenzaldoxime

HRID 49673

반응식

HRID 49673 반응식
[N:1](OCCCC)=[O:2].[N+:8]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[C:12]=1[CH3:18])([O-:10])=[O:9].CC(C)([O-])C.[K+].O>CN(C)C=O.C(O)(=O)C>[CH3:17][C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([N+:8]([O-:10])=[O:9])[C:12]=1[CH:18]=[N:1][OH:2]

참가 물질

7

반응물 4

HCID 962WaterHCID 67391,2-Dimethyl-3-nitrobenzeneHCID 10996Butyl nitriteHCID 23665647Potassium tert-butoxide

생성물 1

HCID 853610482-Methyl-6-nitrobenzaldoxime

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 6228Dimethylformamide용매2회

실험 절차

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.

후처리

  1. additionDuring the addition
  2. customrises to −10° C.
  3. customa yellow suspension is formed
  4. customthe residue that has formed
  5. filtrationis filtered off with suction
  6. washwashed with 5 l of water
  7. customdried in a drying cabinet at 30° C. overnight
  8. customat 80-90° C.
  9. customfor 2 hours
  10. temperatureAfter cooling
  11. filtrationthe product is filtered off with suction
  12. customdried

출처 및 근거

ORD 기록
ord-4b360280ad624c198832b754395490bf
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06706886B2

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