[C:1]([OH:6])(=[O:5])[C:2]([CH3:4])=[CH2:3].C1(C=CC(O)=CC=1)O.[CH:15](O)=[CH:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]>CC1C=CC(S(O)(=O)=O)=CC=1.C1C=CC=CC=1>[C:1]([O:6][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH:16]=[CH2:15])(=[O:5])[C:2]([CH3:4])=[CH2:3]Monomer synthesis. In a 3 neck round bottom flask, methacrylic acid (51.4 g, 0.515 mol) and benzene (60 ml) were combined. P-TSA (0.90 g, 2.6 mmol), hydroquinone (1.56 g, 13.6 mmol) and undecene-1-ol (25.8 g, 0.150 mol) were added into the flask and a Dean Stark adapter was attached. The reaction was heated at reflux overnight. The benzene was removed from the solution by rotary evaporation at reduced pressure and ether (200 ml) was added. NaHCO3 (50 g) was added to the ether solution to remove any excess methacrylic acid. The product was decanted from the NaHCO3 and washed with H2O (200 ml) 3 times, with 5% by weight NaHCO3 (200 ml) solution 3 times, and again with H2O (200 ml) 3 times. The product was dried over MgSO4 and the ether was removed by rotary evaporation. The product was distilled at 110° C. at 150 mTorr to yield 18.3 g (51% yield) of undec-10-enyl methacrylate.
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