[C:1]([OH:6])(=[O:5])[C:2]([CH3:4])=[CH2:3].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:19]=[C:20]1[CH:27]2[CH2:28][CH:23]3[CH2:24][CH:25]([CH2:29][CH:21]1[CH2:22]3)[CH2:26]2.[OH-].[Na+]>C1(C)C=CC=CC=1>[C:1]([O:6][C:20]1([CH3:19])[CH:21]2[CH2:29][CH:25]3[CH2:24][CH:23]([CH2:28][CH:27]1[CH2:26]3)[CH2:22]2)(=[O:5])[C:2]([CH3:4])=[CH2:3]
A 500 ml flask was flushed with nitrogen to displace the air with nitrogen, and was charged with 43.0 g (0.50 mol) of methacrylic acid, 0.95 g (5 mmol) of p-toluenesulfonic acid monohydrate (supplied by Wako Pure Chem. Ind. Ltd.) and 100 g of toluene. Separately 74.0 g (0.50 mol) of 2-methyleneadamantane, prepared by the same procedures as described in Reference Example 1, was dissolved in 100 g of toluene. The obtained solution of 2-methyleneadamantane in toluene was dropwise added to the content in the flask over a period of about 3 hours, while the content was maintained at a reaction temperature of about 5° C. Then the content was stirred for 5 hours at the same temperature. After completion of the reaction, the residual catalyst was neutralized by adding 40.0 g (50 mmol) of a 5% aqueous sodium hydroxide solution, and the neutralized liquid was washed with an aqueous saturated sodium chloride solution. The thus-obtained organic phase was subjected to column chromatography, and further, analyzed by NMR and mass spectrometry. Thus, 106.2 g (yield: 90.8%) of the object 2-methyl-2-adamantyl methacrylate was obtained.
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