N-Hydroxyphthalimide → beta-Nootkatol

Participants

Reaction Conditions

Reaction Steps

In a flask 40.87 g (142 mmol) of valencene with a purity of 71% by weight, 4.89 g (30 mmol) of N-hydroxyphthalimide, 0.49 g (2 mmol) of cobalt(II) acetate tetrahydrate, 1.43 g (4 mmol) of tris(acetylacetonato)cobalt(III), 0.58 g (2 mmol) of cobalt nitrate hexahydrate [Co(NO3)2.6H2O], and 360 g of acetonitrile were placed and were stirred at 40° C. at a pressure of 13 kgf/cm2 (=1.3 MPa) for 3 hours under flow of air at a rate of 11.2 L (under standard conditions) per hour. The reaction mixture was analyzed by gas chromatography and was found that a target compound nootkatone and nootkatol were produced in yields of 67.9% and 5.6%, respectively, with a conversion from valencene of 99%. The reaction mixture was further analyzed by high-performance liquid chromatography and was found to contain 0.04 g of N-hydroxyphthalimide, 0.09 g of phthalimide, and 0.59 g of tris(acetylacetonato)cobalt(III).

Provenance & Evidence