2-(4-Ethenylphenyl)oxirane → p-Divinylbenzene

HRID 1904569Notes

Reaction equation

HRID 1904569 reaction equation
[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([CH:7]2O[CH2:8]2)=[CH:5][CH:4]=1)=[CH2:2].NC(N)=S>CO>[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([CH:7]=[CH2:8])=[CH:5][CH:4]=1)=[CH2:2]

Participants

4

Reactant 2

HCID 1120402-(4-Ethenylphenyl)oxiraneHCID 2723790Thiourea

Product 1

HCID 66041p-DivinylbenzeneYield 67.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

In a one-liter flask equipped with a stirrer and a thermometer was placed 300 ml of methanol. Thereto was added 100 g of 4-vinylstyrene oxide. With keeping the flask inside temperature at 5° to 10° C., 35 g of thiourea was added slowly. The mixture was stirred for 72 hours. After completion of the reaction, methanol was removed by distillation. The concentrate was water-washed to obtain 60 g of 4-vinylstyrene eipsulfide. In the proton NMR spectrum of the product, 4, 1, 1, 1, 1 and 2 protons were observed at δ values of 7.2 to 7.5, 6.65, 5.76, 5.20, 3.95 to 4.15 and 2.8 to 3.0, respectively.

Workup

  1. customIn a one-liter flask equipped with a stirrer
  2. customat 5° to 10° C.
  3. customwas removed by distillation
  4. washwashed

Sources & evidence

ORD record
ord-8134541a57394f12bfeb4d9fbe516d3d
Source dataset
uspto-grants-1989_06
Patent number
US04839261

Reaction notes

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