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

HRID 968046Notes

Reaction equation

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

Participants

Conditions

Temperature: 67.5 °C

Procedure

In a 500 ml round-bottom flask was placed 0.33 mole of 2-(toluene-4-sulfonyloxy)ethyl acrylate, 0.2 mole of 2-hydroxyethyl methacrylate, 0.15 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 ethylether or n-hexane, filtered and dried to provide poly [2-(toluene-4-sulfonyloxy)ethyl acrylate/2-hydroxyethyl methacrylate/-methyl methacrylate/-glycidyl methacrylate] represented by the following chemical formula 6, at a yield of 65-70%.

Workup

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

Sources & evidence

ORD record: ord-aa389fd412014a9fb47ca2e135a317f4
Source dataset: uspto-grants-2005_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06956091B2

Reaction notes

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