N-Hydroxyphthalimide → beta-Nootkatol

참여 물질

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반응 단계

In a flask 316.1 g (1.1 mol) of valencene with a purity of 71% by weight, 22.28 g (0.14 mol) of N-hydroxyphthalimide, 6.97 g (0.028 mol) of cobalt(II) acetate tetrahydrate, 29.93 g (0.084 mol) of tris(acetylacetonato)cobalt(III), and 3230 g of acetonitrile were placed and were stirred at 40° C. at a pressure of 13 kgf/cm2 (=1.3 MPa) for 2 hours under flow of air at a rate of 150 L (under standard conditions) per hour. The resulting mixture was further treated with 22.84 g (0.14 mol) of N-hydroxyphthalimide with stirring at 40° C. for 2 hours. The reaction mixture was analyzed by gas chromatography and was found that a target compound nootkatone and nootkatol were produced in yields of 53.7% and 1.4%, respectively, with a conversion from valencene of 100%. The reaction mixture was further analyzed by high-performance liquid chromatography and was found to contain 4.4 g of N-hydroxyphthalimide, 0.7 g of phthalimide, and 18.8 g of tris(acetylacetonato)cobalt(III).

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