反応 #170953
ord-fd63c91c4c9a443d80e67e9653d27fce
反応方程式
反応物
試薬
反応条件
後処理
- 1その他To a 2 L jacket-equipped separable flask
- 2その他provided with a stirrer
- 3その他Prepared gas
- 4workup.ADDITIONdiluted with nitrogen so as
- 5温度While the solution was heated
- 6その他was removed by the Dean-Stark water separator
- 7その他Thus, 3,5-dihydroxy-1-adamantyl methacrylate was synthesized
- 8その他The obtained reaction solution
- 9洗浄The resultant organic phase was washed with 500 ml of ion exchange water twice
- 10抽出extraction
- 11workup.ADDITIONTo the ethyl acetate solution, 0.76 g of p-methoxyphenol was added as a polymerization inhibitor
- 12workup.DISSOLUTIONdissolved completely
- 13ろ過Precise filtration
- 14ろ過filter
- 15濃縮Then, the resultant solution was concentrated by use of an evaporator while the temperature of the solution
- 16その他was kept at 40° C., until the weight of the solution
- 17濃縮After the concentration
- 18温度cooling
- 19その他crystallization
- 20その他was performed at a temperature of an ice water bath
- 21その他to separate the crystal
- 22ろ過by filtration
- 23洗浄The crystal was rinsed with ion exchange water twice
- 24その他dried at a reduced pressure at 35° C. for 24 hours
- 25その他During the process from the dehydration esterification reaction
- 26その他to the solid-liquid separation
- 27洗浄until the termination of rinsing
実験手順
To a 2 L jacket-equipped separable flask provided with a stirrer, a thermometer, a Dean-Stark water separator, a Dimroth condenser and a prepared gas introduction tube, 128.9 g of 1,3,5-adamantanetriol, 361 g of methacrylic acid, 1.7 g of concentrated sulfuric acid as an acid catalyst, 1.1 g of p-methoxyphenol as a polymerization inhibitor, and 750 ml of toluene as a solvent were put. Prepared gas diluted with nitrogen so as to have an oxygen concentration of about 5% by volume was supplied at a rate of 0.2 L/min. The reaction operation was performed as follows. While the solution was heated and water generated as a secondary product was removed by the Dean-Stark water separator, the reflux state was continued for 12 hours. Thus, 3,5-dihydroxy-1-adamantyl methacrylate was synthesized. The obtained reaction solution was cooled down to room temperature, and then a 10% by weight of aqueous solution of sodium hydroxide was added while stirring to neutralize the residual methacrylic acid and sulfuric acid. Then, the neutralized water phase was drawn out from the two-phase solution. The resultant organic phase was washed with 500 ml of ion exchange water twice. After the water phase was all united, extraction was performed with 300 ml of ethyl acetate twice. To the ethyl acetate solution, 0.76 g of p-methoxyphenol was added as a polymerization inhibitor and dissolved completely. Precise filtration was performed by use of a Teflon® filter having a pore diameter of 0.1 μm. Then, the resultant solution was concentrated by use of an evaporator while the temperature of the solution was kept at 40° C., until the weight of the solution became 110 g. After the concentration was finished, cooling crystallization was performed at a temperature of an ice water bath to separate the crystal by filtration. The crystal was rinsed with ion exchange water twice, and then dried at a reduced pressure at 35° C. for 24 hours. During the process from the dehydration esterification reaction to the solid-liquid separation and until the termination of rinsing performed by use of ion exchange water, the prepared gas was kept blown into the solution. Table 1 shows the analysis results of the obtained 3,5-dihydroxy-1-adamantyl methacrylate. Tetrahydrofuran was used as the solvent for measuring the turbidity.