4-Vinylphenol → 4-Ethynylphenol

HRID 1384432Notes

Reaction equation

HRID 1384432 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)=[CH2:2]>C1(C)C=CC(S(O)(=O)=O)=CC=1.C(#N)C>[CH:2]#[C:1][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1

Participants

4

Reactant 1

HCID 624534-Vinylphenol

Product 1

HCID 327584-EthynylphenolYield 17.1%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 6342AcetonitrileSolvent2×

Procedure

50.5 g of the same p-vinylphenol fraction as used in Example 1, obtained by vacuum flash distillation was placed in a 300-ml flask together with 50.5 g of acetonitrile. To the resulting mixture being stirred was dropwise added 0.3 ml of an acetonitrile solution containing 0.03 g of p-toluenesulfonic acid. A polymerization reaction was conducted for 1 hour in the same manner as in Example 1 to obtain 8.5 g of a poly(p-vinylphenol). The polymer had a Mw of 15,000, a Mn of 11,500, a light transmittance at 248 nm, of 75.5% and a light transmittance at 450 nm, of 95.4%.

Workup

  1. customobtained by vacuum flash distillation
  2. customA polymerization reaction

Sources & evidence

ORD record
ord-2f5c2afa7d2846229bf4e588cc8307b8
Source dataset
uspto-grants-2001_07
Patent number
US06258901B1

Reaction notes

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