2-Hydroxyethyl Methacrylate → 1-Cyclohexyloxyethyl methacrylate 3,4-epoxycyclohexylmethyl methacrylate 2-hydroxyethyl methacrylate

HRID 2191185Notes

Reaction equation

HRID 2191185 reaction equation
[C:1]([O:6][CH:7]([O:9][CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)[CH3:8])(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:16]([O:21][CH2:22][CH:23]1[CH2:28][CH2:27][CH:26]2[O:29][CH:25]2[CH2:24]1)(=[O:20])[C:17]([CH3:19])=[CH2:18].[C:30]([O:35][CH2:36][CH2:37][OH:38])(=[O:34])[C:31]([CH3:33])=[CH2:32].N(C(C)(CC)C([O-])=O)=NC(C)(CC)C([O-])=O>CCCCCCC.C(C(C)=O)C(C)C>[C:1]([O:6][CH:7]([O:9][CH:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1)[CH3:8])(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:16]([O:21][CH2:22][CH:23]1[CH2:28][CH2:27][CH:26]2[O:29][CH:25]2[CH2:24]1)(=[O:20])[C:17]([CH3:19])=[CH2:18].[C:30]([O:35][CH2:36][CH2:37][OH:38])(=[O:34])[C:31]([CH3:33])=[CH2:32]

Participants

7

Reactant 4

HCID 133602-Hydroxyethyl MethacrylateHCID 14645478(7-Oxabicyclo(4.1.0)heptan-3-yl)methyl 2-methylprop-2-enoateHCID 219175032,2'-Azobis(methyl 2-methylpropanate)HCID 229952811-Cyclohexyloxyethyl methacrylate

Product 1

HCID 866432101-Cyclohexyloxyethyl methacrylate 3,4-epoxycyclohexylmethyl methacrylate 2-hydroxyethyl methacrylate

Reagents, catalysts & solvents 2

HCID 7909Methyl Isobutyl KetoneSolventHCID 8900HeptaneSolvent

Procedure

Into a 500 ml-volume three-neck flask, 76.4 g (0.36 mol) of 1-cyclohexyloxyethyl methacrylate, 35.3 g (0.18 mol) of 3,4-epoxycyclohexylmethyl methacrylate (Cyclomer M100, produced by Daicel Chemical Industries, Ltd.), 7.8 g (0.06 mol) of 2-hydroxyethyl methacrylate and 300 ml of methyl isobutyl ketone were charged. A catalytic amount of 2,2′-azobis(methyl 2-methylpropionate) was added thereto as a radical polymerization initiator, and polymerization was allowed to proceed at 80° C. for 6 hours in a nitrogen stream. The reaction solution was cooled and then poured in a large amount of heptane to precipitate a polymer. The crystal was collected by filtration and dissolved in diethylene glycol dimethyl ether, and heptane and methyl isobutyl ketone contained in the solution were removed by distillation under reduced pressure to obtain Polymer A-5 (1-cyclohexyloxyethyl methacrylate/3,4-epoxycyclohexylmethyl methacrylate/2-hydroxyethyl methacrylate) as a diethylene glycol dimethyl ether solution.

Workup

  1. customas a radical polymerization initiator, and polymerization
  2. temperatureThe reaction solution was cooled
  3. customto precipitate a polymer
  4. filtrationThe crystal was collected by filtration
  5. dissolutiondissolved in diethylene glycol dimethyl ether
  6. customwere removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-effc43291b5a4d58bf5cfcb7ee348b26
Source dataset
uspto-grants-2012_12
Patent number
US08329380B2

Reaction notes

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