Water → 1-Cyano-2-methyl-3-prop-2-enylbenzene

HRID 1656929

반응식

HRID 1656929 반응식
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH:9]=[CH2:10])[C:3]=1[CH3:11].[Cu][C:13]#[N:14].C(N)CN.O>CN1CCCC1=O>[C:13]([C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH:9]=[CH2:10])[C:3]=1[CH3:11])#[N:14]

참가 물질

6

반응물 4

HCID 962WaterHCID 3301EthylenediamineHCID 106786531-Chloro-2-methyl-3-prop-2-enylbenzeneHCID 178418546HCID 178418546, 화합물

생성물 1

HCID 197864851-Cyano-2-methyl-3-prop-2-enylbenzene수율 50.9%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
190 °C

실험 절차

30 g of 1-chloro-2-methyl-3-prop-2-enylbenzene are dissolved in 150 ml of N-methylpyrrolidone, and 25 g of copper(I) cyanide are added. The reaction mixture is heated at 190° C. for 30 hours while stirring. After the mixture has been cooled to 20° C., 125 ml of ethylenediamine and 300 ml of water are added. Stirring is then carried out for 1 hour at 50° C. and for 14 hours at 20° C. Working up is effected by extracting with diethyl ether, washing the organic phase and drying over sodium sulfate, removing the drying agent and distilling off the organic solvent. 24.5 g of crude product are obtained. After chromatography (silica gel/toluene), 14.4 g of pure 1-cyano-2-mehtyl-3-prop-2-enylbenzene are isolated.

후처리

  1. temperatureAfter the mixture has been cooled to 20° C.
  2. stirringStirring
  3. extractionby extracting with diethyl ether
  4. washwashing the organic phase
  5. dry with materialdrying over sodium sulfate
  6. customremoving the drying agent
  7. distillationdistilling off the organic solvent
  8. custom24.5 g of crude product are obtained

출처 및 근거

ORD 기록
ord-a303102d4c8248989303cabd7d70b551
출처 데이터셋
uspto-grants-1993_10
특허 번호
US05256666

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