Azobisisobutyronitrile → 2-(Toluene-4-sulfonyloxy)ethyl acrylate 3-hydroxypropyl acrylate

HRID 968047Notes

Reaction equation

HRID 968047 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:23][CH2:24][CH2:25][CH2:26][OH:27])(=[O:22])[CH:20]=[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:23][CH2:24][CH2:25][CH2:26][OH:27])(=[O:22])[CH:20]=[CH2:21]

Participants

7

Reactant 5

HCID 6547AzobisisobutyronitrileHCID 6658Methyl MethacrylateHCID 7837Glycidyl methacrylateHCID 331012-Propenoic acid, 3-hydroxypropyl esterHCID 222922512-(Toluene-4-sulfonyloxy)ethyl acrylate

Product 1

HCID 867598712-(Toluene-4-sulfonyloxy)ethyl acrylate 3-hydroxypropyl acrylateYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
67.5 °C

Procedure

In a 500 ml round-bottom flask was placed 0.3 mole of 2-(toluene-4-sulfonyloxy)ethyl acrylate, 0.25 mole of 3-hydroxypropyl 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 precipitated in ethyl ether or n-hexane, filtered and dried to provide poly [2-(toluene-4-sulfonyloxy)ethyl acrylate/3-hydroxypropyl acrylate/-methyl methacrylate/-glycidyl methacrylate] represented by the following chemical formula 7, at a yield of 65-70%.

Workup

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

Sources & evidence

ORD record
ord-65c14325a10648e395442cdade37011b
Source dataset
uspto-grants-2005_10
Patent number
US06956091B2

Reaction notes

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