N-Hydroxyphthalimide → beta-Nootkatol

HRID 495708

Reaktionsgleichung

C[C@H]1[C@]2(C)C[C@H](C(C)=C)CCC2=CCC1.ON1C(=O)C2=CC=CC=C2C1=O.[CH3:28][C@H:29]1[C@:35]2([CH3:43])[CH2:36][C@H:37]([C:40]([CH3:42])=[CH2:41])[CH2:38][CH2:39][C:34]2=[CH:33][C:31](=[O:32])[CH2:30]1>O.O.O.O.C([O-])(=O)C.[Co+2].C([O-])(=O)C.CC(CC(C)=O)=O.CC(CC(C)=O)=O.CC(CC(C)=O)=O.[Co].C(#N)C>[CH3:28][C@H:29]1[C@:35]2([CH3:43])[CH2:36][C@H:37]([C:40]([CH3:42])=[CH2:41])[CH2:38][CH2:39][C:34]2=[CH:33][C@@H:31]([OH:32])[CH2:30]1

Komponenten

Reaktionsbedingungen

Temperatur: 40 °C

Versuchsvorschrift

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).

Aufarbeitung

stirringwith stirring at 40° C. for 2 hours

Quellen und Nachweise

ORD-Eintrag: ord-7b13898ce0894e518e28ccbda6c1d886
Quelldatensatz: uspto-grants-2005_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06939993B2

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