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

HRID 1656929

Reaction equation

HRID 1656929 reaction equation
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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
190 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a303102d4c8248989303cabd7d70b551
Source dataset
uspto-grants-1993_10
Patent number
US05256666

Linked notes

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