Acetone → Styrene

HRID 1957296

Reaction equation

HRID 1957296 reaction equation
[C:1]1([CH3:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[S-:8][C:9]#[N:10].[K+].[CH3:12][C:13]([CH3:15])=O>CN(C=O)C>[CH2:9]=[CH:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[S:8]([CH2:12][C:13]1[CH:15]=[CH:7][C:1]([CH:6]=[CH2:5])=[CH:2][CH:3]=1)[C:9]#[N:10]

Participants

6

Reactant 3

HCID 180AcetoneHCID 1140TolueneHCID 516872Potassium thiocyanate

Product 2

HCID 7501StyreneHCID 15217596(4-Ethenylphenyl)methyl thiocyanate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The desired terpolymer of styrene, 4-thiocyanatomethylstyrene, and vinyl benzyl polyethylene glycol was synthesized from the terpolymer of Step II as follows: 1.5 g of the terpolymer formed in Step II was mixed with 350 mL of toluene taken in a 500 mL flask and the contents stirred. To this mixture was added 1.2 g of potassium thiocyanate dissolved in 115 mL of a solvent mixture of DMF and acetone (100/15, v/v). The entire contents of the flask was then heated and allowed to reflux for about 30 hours. The contents were then allowed to cool to room temperature at which time slightly turbid mixture became homogeneous. The solvents were evaporated under vacuo and the residual solids were precipitated from water. The precipitate was washed with methanol and dried to yield a white powder of the terpolymer (0.9 g). The structure of the produced terpolymer was verified by 1H and 13C NMR, and IR spectroscopy.

Workup

  1. custom1.5 g of the terpolymer formed in Step II
  2. customtaken in a 500 mL flask
  3. temperatureThe entire contents of the flask was then heated
  4. temperatureto reflux for about 30 hours
  5. customThe solvents were evaporated under vacuo
  6. customthe residual solids were precipitated from water
  7. washThe precipitate was washed with methanol
  8. customdried
  9. customto yield a white powder of the terpolymer (0.9 g)

Sources & evidence

ORD record
ord-7d2143a943d94d98a9729ee266470cf9
Source dataset
uspto-grants-1998_07
Patent number
US05783648

Linked notes

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