Hydroquinone → Vinylphenol tert-butyl methacrylate 2-vinylnaphthalene

HRID 1757026Notes

Reaction equation

[CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9])=[CH2:2].[C:10]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])(=[O:14])[C:11]([CH3:13])=[CH2:12].[CH:20]([C:22]1[CH:31]=[CH:30][C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=1)=[CH2:21].CC(N=NC(C#N)(C)C)(C#N)C.C1(C=CC(O)=CC=1)O.C(C1C2C(=CC=CC=2)C=CC=1)=C>C1(C)C=CC=CC=1>[CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9])=[CH2:2].[C:10]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])(=[O:14])[C:11]([CH3:13])=[CH2:12].[CH:20]([C:22]1[CH:31]=[CH:30][C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=1)=[CH2:21]

Participants

Conditions

Temperature: 80 °C

Procedure

5.54 g (0.05 mol) of vinylphenol, 5.47 g (0.04 mol) of tert-butyl methacrylate, 2.37g (0.02 mol) of 2-vinylnaphthalene and 0.8205 g (5 mol %) of AIBN were charged into 50g (1.7 M) of toluene. After the mixture was stirred at 80° C. for 11 hours, hydroquinone was added and the polymerization was stopped. Toluene was evaporated by an evaporator to prepare a THF solution, and reprecipitation was repeated using cyclohexane. The polymer thus refined was dried in a vacuum baking oven at 40° C. for 14 hours. There was obtained a polymer having a molecular weight of 12,000, a degree of dispersion of 1.87 and a vinylphenol:tert-BuMA:vinylnaphthalene ratio of 52:43:18.

Workup

customToluene was evaporated by an evaporator
customto prepare
customa THF solution, and reprecipitation
customThe polymer thus refined was dried in a vacuum baking oven at 40° C. for 14 hours
customThere was obtained a polymer

Sources & evidence

ORD record: ord-54006827c7ed4a78a00ff36a4c140926
Source dataset: uspto-grants-1995_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05443690

Reaction notes

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