[CH:1]12[CH2:7][CH:4]([CH:5]=[CH:6]1)[CH2:3][CH:2]2[CH2:8][OH:9].[C:10](OC)(=[O:14])[C:11]([CH3:13])=[CH2:12].C1(C=CC(O)=CC=1)O.C[O-].[Na+]>CN(C)C=O.O>[C:10]([O:9][CH2:8][CH:2]1[CH2:3][CH:4]2[CH2:7][CH:1]1[CH:6]=[CH:5]2)(=[O:14])[C:11]([CH3:13])=[CH2:12]
5-norbornen-2-ylmethyl methacrylate monomer was prepared in a flask fitted with a vertical condenser with water at 75° C circulating through the jacket, attached at the top to a downwards cold water-cooled condenser. There were refluxed for 2 hours 372 grams (3.0 moles) of 5-norbornen -2-methanol, 450 grams (4.5 moles) of methyl methacrylate, 526 grams of N,N-dimethylformamide, 28.8 grams of hydroquinone, and 8.1 grams (0.15 mole) of sodium methoxide. A total of 252 ml of distillate was collected (theoretical methanol equals 121 ml.). The flask contents were cooled, diluted with ether, and washed with water, excess dilute hydrochloric acid, water, 5% aqueous sodium hydroxide until the washes were colorless, and again with water. The ether solution was dried with anhydrous sodium sulfate, 11.5 grams of p-(p-tolylsulfonyl-amido) diphenylamine were added, and the ether was removed in a rotary evaporator at 60° C and about 15 mm pressure. To the residual oil 0.58 gram of hydroquinone was added and the product was distilled through a Vigreux column to give 431 grams of product having a boiling point of 770 C/1.4 mm, nD20 = 1.4848. The monomer was then passed through a column of activated sodium aluminum silicate.
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