Benzene, (2-chloroethoxy)- → 2-(4-Chlorophenyl)-4-phenoxybutanenitrile

HRID 260342

반응식

HRID 260342 반응식
[H-].[Na+].[Cl:3][C:4]1[CH:12]=[CH:11][C:7]([CH2:8][C:9]#[N:10])=[CH:6][CH:5]=1.Cl[CH2:14][CH2:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C=O)C>[Cl:3][C:4]1[CH:12]=[CH:11][C:7]([CH:8]([CH2:14][CH2:15][O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:9]#[N:10])=[CH:6][CH:5]=1

참가 물질

5

반응물 3

HCID 12156Benzene, (2-chloroethoxy)-HCID 24758Sodium hydrideHCID 2415824-Chlorobenzyl cyanide

생성물 1

HCID 224014342-(4-Chlorophenyl)-4-phenoxybutanenitrile수율 96%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a flask was added 7.2 g. (0.150 mole) of a 50% oil dispersion of sodium hydride. After washing the sodium hydride several times with hexane to remove the mineral oil, 18.9 g. (0.125 mole) of 4-chlorobenzyl cyanide in 50 ml of dry DMF was added dropwise at 0° C. Upon completion of the addition, the reaction was stirred for one hour while warming to room temperature, then 20.0 g. (0.128 mole) of 1-chloro-2-phenoxyethane was added dropwise at 15° C. over a 30 minute period. The stirred reaction was allowed to warm to room temperature and was complete in two hours. The reaction mixture was diluted with 300 ml. of water and extracted three times with 100 ml. portions of methylene chloride. The combined extracts were washed with dilute hydrochloric acid and water followed by drying using sodium sulfate. Upon removal of the solvent, 33 g. of the crude 2-(4-chlorophenyl)-4-phenoxybutanenitrile was obtained (96% yield).

후처리

  1. additionTo a flask was added 7.2 g
  2. washAfter washing the sodium hydride several times with hexane
  3. customto remove the mineral oil, 18.9 g
  4. additionUpon completion of the addition
  5. customThe stirred reaction
  6. temperatureto warm to room temperature
  7. waitwas complete in two hours
  8. additionThe reaction mixture was diluted with 300 ml
  9. extractionof water and extracted three times with 100 ml
  10. washThe combined extracts were washed with dilute hydrochloric acid and water
  11. customby drying
  12. customUpon removal of the solvent, 33 g

출처 및 근거

ORD 기록
ord-8c84c1bffeec4cccbbb4be07a6dc021c
출처 데이터셋
uspto-grants-1996_06
특허 번호
US05527816

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