Ethylbenzene → HCID 53693694, compound

HRID 2050783Notes

Reaction equation

HRID 2050783 reaction equation
C([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]=[CH2:10])=C.C([C:13]1[CH:18]=[CH:17][CH:16]=CC=1)C.C(C1C=CC=C(C=C)C=1)=C.C(C1C=CC(C=C)=CC=1)=C.[CH2:39]([NH:43][CH2:44][CH2:45]CC)[CH2:40][CH2:41][CH3:42].C([Li])CCC>C1CCCCC1.CO>[CH2:39]([N:43]([CH2:44][CH2:45][CH:10]=[CH:9][C:4]1[CH:3]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH2:16][CH2:17][CH2:18][CH3:13])[CH2:40][CH2:41][CH3:42]

Participants

9

Reactant 6

HCID 7500EthylbenzeneHCID 79411,3-DiethenylbenzeneHCID 8148DibutylamineHCID 66041p-DivinylbenzeneHCID 666661,2-DiethenylbenzeneHCID 178418339Butyllithium

Product 1

HCID 53693694HCID 53693694, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8078CyclohexaneSolvent

Conditions

Temperature
50 °C

Procedure

In 100 ml of cyclohexane was dissolved 65.0 g of divinylbenzene (a 55% ethylbenzene solution of a mixture of m-divinylbenzene and p-divinylbenzene) and after adding dropwise thereto an amine-amide complex composed of 64.5 g of di-n-butylamine and 25 mmoles of n-butyl lithium, the mixture was heated to 50° C. for 3 hours. To the reaction mixture was added 1 ml of methanol. After concentrating the mixture, 1 g of di-tert-butylcatechol was added to the residue, and then the resultant mixture was distilled under reduced pressure to provide 53.5 g of (di-n-butylaminoethyl)styrene (a colorless liquid having a boiling point of 100.0°-101.0° C./1 mm Hg).

Workup

  1. additionafter adding dropwise
  2. concentrationAfter concentrating the mixture, 1 g of di-tert-butylcatechol
  3. additionwas added to the residue
  4. distillationthe resultant mixture was distilled under reduced pressure

Sources & evidence

ORD record
ord-aa0881a3d14f430381a50d0db628f9de
Source dataset
uspto-grants-1991_05
Patent number
US05015551

Reaction notes

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