Azobisisobutyronitrile → 2-(Toluene-4-sulfonyloxy)ethyl methacrylate 4-hydroxybutyl acrylate

HRID 968053Notes

Reaction equation

[C:1]([O:6][CH2:7][CH2:8][O:9][S:10]([C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)(=[O:12])=[O:11])(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:20]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][OH:29])(=[O:23])[CH:21]=[CH2:22].C(OC)(=O)C(C)=C.C(OCC1OC1)(=O)C(C)=C.CC(N=NC(C#N)(C)C)(C#N)C>O1CCCC1>[C:1]([O:6][CH2:7][CH2:8][O:9][S:10]([C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)(=[O:11])=[O:12])(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:20]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][OH:29])(=[O:23])[CH:21]=[CH2:22]

Participants

Conditions

Temperature: 67.5 °C

Procedure

In a 500 ml round-bottom flask was placed 0.3 mole of 2-(toluene-4-sulfonyloxy)ethyl methacrylate, 0.2 mole of 4-hydroxybutyl acrylate, 0.1 mole of methyl methacrylate, 0.3 mole of glycidyl methacrylate, 300 g of tetrahydrofuran (THF), and 0.1 g-3 g of AIBN. The reaction mixture was heated at 60-75° C. for 5-20 hours. The product was precipitated in ethyl ether or n-hexane, filtered and dried to provide poly [2-(toluene-4-sulfonyloxy)ethyl methacrylate/4-hydroxybutyl acrylate-/methyl methacrylate-/glycidyl methacrylate] represented by the following chemical formula 14, at a yield of 65-70%.

Workup

customIn a 500 ml round-bottom flask was placed
customThe product was precipitated in ethyl ether
filtrationn-hexane, filtered
customdried

Sources & evidence

ORD record: ord-aa10fa8eeee4476c8a357675d97125bb
Source dataset: uspto-grants-2005_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06956091B2

Reaction notes

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