Dimethylformamide → 1,12-Bis(3,4-dicyanophenoxy) dodecane

HRID 903120

反応式

HRID 903120 の反応式
[CH2:1]([OH:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13].[H-].[Na+].C[N:18]([CH3:21])C=O.[N+]([C:25]1[CH:26]=[C:27]([C:33]#[N:34])[C:28](=[CH:31][CH:32]=1)[C:29]#[N:30])([O-])=O>O>[C:29]([C:28]1[CH:27]=[C:26]([CH:25]=[CH:32][C:31]=1[C:21]#[N:18])[O:14][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:25]1[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[C:27]([C:33]#[N:34])[CH:26]=1)#[N:30]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 797581,12-DodecanediolHCID 974431,2-Benzenedicarbonitrile, 4-nitro-2 回

生成物 1

HCID 125786551,12-Bis(3,4-dicyanophenoxy) dodecane収率 40%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A mixture of 1,12-dodecanediol (2,2 g, 0.011 mol), sodium hydride (0.91 g. 0.023 mol, 61%) and 25 ml of dry dimethylformamide were stirred under a nitrogen atmosphere at 90°-95° C. for 12 hours. After cooling, 4.0 g (0.23 mol) of 4-nitrophthalonitrile was added to the white salt mixture. The salt dissolved quickly and the mixture was heated at 100°-110° C. for 4 hours. Infrared analysis indicated that a large quantity of 4-nitrophthalonitrile was still present. The temperature was increased to 140°-145° C. and the mixture was stirred at this temperature for 15 hours. The cooled reaction mixture was poured into 200 ml of cold water and the product was extracted into three, 75 ml portions of methylene chloride. The combined extract was washed several times with water, charcoaled, dried over anhydrous sodium sulfate, and concentrated at reduced pressure. Recrystallization of the crude material from ethanol-water yielded 1.7 g (40%) of 1,12-bis(3,4-dicyanophenoxy) dodecane.

後処理

  1. temperatureAfter cooling
  2. dissolutionThe salt dissolved quickly
  3. temperaturethe mixture was heated at 100°-110° C. for 4 hours
  4. temperatureThe temperature was increased to 140°-145° C.
  5. stirringthe mixture was stirred at this temperature for 15 hours
  6. customThe cooled reaction mixture
  7. extractionthe product was extracted into three, 75 ml portions of methylene chloride
  8. extractionThe combined extract
  9. washwas washed several times with water
  10. dry with materialdried over anhydrous sodium sulfate
  11. concentrationconcentrated at reduced pressure
  12. customRecrystallization of the crude material from ethanol-water

出典と根拠

ORDレコード
ord-c56a6c3894b94cabb39d82ab0a14f534
出典データセット
uspto-grants-1980_10
特許番号
US04226801

関連ノート

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