Azobisisobutyronitrile → 4-Ethynylphenol

HRID 1492876Notes

Reaction equation

HRID 1492876 reaction equation
C([O:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[CH2:11])=[CH:8][CH:7]=1)(C)(C)C.N(C(C)(C)C#N)=NC(C)(C)C#N>O1CCOCC1>[CH:11]#[C:10][C:9]1[CH:12]=[CH:13][C:6]([OH:5])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 6547AzobisisobutyronitrileHCID 5775311-(Tert-butoxy)-4-ethenylbenzene

Product 1

HCID 327584-Ethynylphenol

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

In 100 ml of dioxane were dissolved 176 g (1.0 mole) of p-t-butoxystyrene and 8.2 g (0.05 mole) of azobisisobutyronitrile, and the resulting solution was subjected to reaction for 24 hours while the internal temperature was kept at 70° C., after which the reaction mixture was subjected to several reprecipitation treatments to remove the unreacted monomer, thereby obtaining poly(p-t-butoxystyrene). Subsequently, this poly(p-t-butoxystyrene) was hydrolyzed with an acid to obtain poly(p-hydroxystyrene) having a Mw of 30,000. This resin is referred to hereafter as Resin A1.

Workup

  1. customthe resulting solution was subjected to reaction for 24 hours while the internal temperature
  2. customwas kept at 70° C.
  3. customafter which the reaction mixture was subjected to several reprecipitation treatments
  4. customto remove the unreacted monomer

Sources & evidence

ORD record
ord-b62eb3753b7742e98f7328b298261ac3
Source dataset
uspto-grants-1994_12
Patent number
US05376498

Reaction notes

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