N-Hydroxyphthalimide → beta-Nootkatol

HRID 495709

Reaction equation

HRID 495709 reaction equation
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].O.O.O.O.O.O.[N+]([O-])([O-])=O.[Co+2].[N+]([O-])([O-])=O.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

Participants

8

Reactant 3

HCID 10665N-HydroxyphthalimideHCID 1268142(+)-NootkatoneHCID 9855795Valencene

Product 1

HCID 182645beta-Nootkatol

Reagents, catalysts & solvents 4

HCID 24821Cobaltous nitrate hexahydrateCatalystHCID 61372Cobalt(II) acetate tetrahydrateCatalystHCID 407384Cobalt(3+) acetylacetonateCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

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).

Sources & evidence

ORD record
ord-b931090ac9f04cddbcfaf0d0c2d547ff
Source dataset
uspto-grants-2005_09
Patent number
US06939993B2

Linked notes

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