Methanol → 2-ethyl-2-adamantyl Methacrylate p-acetoxystyrene

HRID 2120033

Reaction equation

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

Participants

Conditions

Temperature: 75 °C

Procedure

Into a flask were charged 59.6 g (0.24 mol) of 2-ethyl-2-adamantyl methacrylate, 90.8 g (0.56 mol) of p-acetoxystyrene and 279 g of isopropanol, and the mixture was heated up to 75° C. under a nitrogen atmosphere. Into this solution was dropped a solution prepared by dissolving 11.05 g (0.048 mol) of dimethyl 2,2′-azobis(2-methylpropionate) in 22.11 g of isopropanol. The mixture was aged for about 0.3 hours at 75° C., and for about 12 hours under reflux, then, diluted with acetone, and the reaction solution was poured into a large amount of methanol, to precipitate a polymer which was filtrated. The amount of the resulted copolymer of 2-ethyl-2-admantyl methacrylate and p-acetoxystyrene was 250 g (weight of wet cake containing methanol).

Workup

additionInto this solution was dropped a solution
customprepared
temperaturefor about 12 hours under reflux
customto precipitate a polymer which
filtrationwas filtrated
addition250 g (weight of wet cake containing methanol)

Sources & evidence

ORD record: ord-a5195ef4feb94663be4fbb672a03aec9
Source dataset: uspto-grants-2004_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06689531B2

Linked notes

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