4-Vinylphenol → 4-Ethynylphenol

HRID 1384429Notes

Reaction equation

HRID 1384429 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)=[CH2:2]>C(#N)C>[CH:2]#[C:1][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1

Participants

3

Reagents, catalysts & solvents 1

Procedure

The same crude p-vinylphenol as used in Example 1 was subjected to azeotropic distillation with toluene without being subjected to vacuum flash distillation, to reduce the water content to 0.038%. A polymerization reaction was conducted in the same manner as in Example 1 except that 28.8 g of acetonitrile was added to 32.3 g of the above-obtained fraction. The reaction mixture was purified by the same reprecipitation as in Example 1, and the resulting precipitate was dried to obtain 6.5 g of a yellowish brown poly(p-vinylphenol). The polymer had a weight-average molecular weight (Mw) of 20,400, a number-average molecular weight (Mn) of 11,500, a light transmittance at a wavelength of 248 nm, of 68.0%, a light transmittance at a wavelength of 450 nm, of 83.2%, and a glass transition temperature of 177° C.

Workup

  1. distillationwas subjected to azeotropic distillation with toluene
  2. distillationwithout being subjected to vacuum flash distillation
  3. customA polymerization reaction
  4. additionwas added to 32.3 g of the above-obtained fraction
  5. customThe reaction mixture was purified by the same reprecipitation as in Example 1
  6. customthe resulting precipitate was dried

Sources & evidence

ORD record
ord-9756f22c3ac3484eaae81b76f10c3555
Source dataset
uspto-grants-2001_07
Patent number
US06258901B1

Reaction notes

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