3-Methylbicyclo(2.2.1)heptane-2-methanol → Santene

関与物質

反応手順

In accordance with the same procedures as those conducted in Example 26, 2,200 g of a dehydration product of 2-hydroxymethyl-3-methylbicyclo[2.2.1]heptane containing 2-methylene-3-methylbicyclo-[2.2.1]heptane and 2,3-dimethylbicyclo[2.2.1]hept-2-ene was obtained. The obtained product was placed into a 5 liter four-necked flask in combination with 45 g of boron trifluoride diethyl etherate. The dimerization was conducted for 5 hours under stirring at 10° C. After the reaction mixture was washed with a dilute aqueous solution of NaOH and a saturated aqueous solution of sodium chloride, the unreacted olefin was removed by distillation, and a reaction mixture of the dimerization of the raw material was obtained. The dimer of the olefin in an amount of 1,500 g was placed into a 2 liter autoclave and heated at 300° C. for 7 hours under stirring. After the reaction mixture was cooled, 30 g of a nickel/diatomaceous earth catalyst for hydrogenation (manufactured by NIKKI CHEMICAL Co., Ltd.; “N-113”) was added, and the hydrogenation was conducted (the hydrogen pressure: 30 kg/cm2; the reaction temperature: 250° C.; the reaction time: 5 hours). After the reaction was completed, the catalyst was removed by filtration. The filtrate was rectified under a reduced pressure, and 155 g of methylcyclopentylmethyl-dimethylbicyclo[2.2.1]heptane was obtained as a fraction having a boiling point in the range of 127 to 130° C./68 mmHg. The results of the measurements of the properties and the traction coefficient of the fluid are shown in Table 9.

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