Dimethylformamide → 3-(2,5-Dimethyl-5-hexene-3-oxy)phthalonitrile

HRID 1289346

반응식

HRID 1289346 반응식
[H-].[Na+].CN(C)C=O.[CH3:8][CH:9]([CH:11]([OH:16])[CH2:12][C:13]([CH3:15])=[CH2:14])[CH3:10].[N+]([C:20]1[CH:27]=[CH:26][CH:25]=[C:22]([C:23]#[N:24])[C:21]=1[C:28]#[N:29])([O-])=O>C1(C)C=CC=CC=1.O>[CH3:8][CH:9]([CH:11]([O:16][C:20]1[CH:27]=[CH:26][CH:25]=[C:22]([C:23]#[N:24])[C:21]=1[C:28]#[N:29])[CH2:12][C:13]([CH3:15])=[CH2:14])[CH3:10]

참가 물질

7

반응물 4

HCID 6228Dimethylformamide2회HCID 24758Sodium hydrideHCID 1442642,5-Dimethyl-5-hexen-3-olHCID 1626521,2-Benzenedicarbonitrile, 3-nitro-

생성물 1

HCID 189210253-(2,5-Dimethyl-5-hexene-3-oxy)phthalonitrile수율 86%

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매

실험 절차

9.6 g (0.24 mol) of 60% sodium hydride and 150 ml of N,N-dimethylformamide were placed in a container equipped with a stirrer, a reflux condenser and a nitrogen-introducing tube, and the solution was then stirred under the feed of nitrogen. Afterward, 32 g (0.25 mol) of 2,5-dimethyl-5-hexene-3-ol was added dropwise thereto at 20°-30° C. over 1 hour, and the solution was then stirred at the same temperature for 3 hours to prepare a sodium alcoholate solution. Next, 34.6 g (0.2 mol) of 3-nitrophthalonitrile and 150 ml of N,N-dimethylformamide were placed in a container equipped with a stirrer, and the above-mentioned sodium alcoholate solution was then added dropwise at 0° C. or less over 5 hours. After completion of the addition, the temperature of the solution was raised up to a level of 20°-30° C., and the solution was then stirred for 2 hours to bring reaction to an end. The thus obtained reaction solution was poured into 3 l of water and then stirred for 30 minutes, and 500 ml of toluene were added. After stirring for 30 minutes, the solution was allowed to stand to separate a toluene layer. After toluene was distilled off under reduced pressure, recrystallization was carried out from 500 ml of n-hexane to obtain 43.7 g of 3-(2,5-dimethyl-5-hexene-3-oxy)phthalonitrile (yield =86.0%).

후처리

  1. customequipped with a stirrer, a reflux condenser
  2. additiona nitrogen-introducing tube
  3. stirringthe solution was then stirred at the same temperature for 3 hours
  4. customequipped with a stirrer
  5. additionAfter completion of the addition
  6. temperaturethe temperature of the solution was raised up to a level of 20°-30° C.
  7. stirringthe solution was then stirred for 2 hours
  8. customreaction to an end
  9. customThe thus obtained reaction solution
  10. stirringstirred for 30 minutes
  11. stirringAfter stirring for 30 minutes
  12. customto separate a toluene layer
  13. distillationAfter toluene was distilled off under reduced pressure, recrystallization

출처 및 근거

ORD 기록
ord-ee0c4eff8678454d9eb4eb5ad607ce67
출처 데이터셋
uspto-grants-1998_05
특허 번호
US05750229

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