Oct-2-ene → 1-Tetralone

HRID 1976864

Reaktionsgleichung

Reaktionsgleichung von HRID 1976864
[CH3:1]/[CH:2]=C\CCCCC.[CH2:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11][CH2:10]1.[OH:19]N1[C:24](=O)[C:23]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:22]2[C:21]1=[O:30].CC=CCCCCC.O1C(CCCCC)C1C>[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Mo].C([O-])(=O)C.[Co+2].C([O-])(=O)C.C(#N)C1C=CC=CC=1>[CH2:16]1[CH2:17][C:18]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:14]([OH:19])[CH2:15]1.[CH2:1]1[CH2:2][C:21](=[O:30])[C:22]2[C:23](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:24]1

Komponenten

10

Edukt 5

HCID 8126Oct-2-eneHCID 8404Tetralin2×HCID 10665N-HydroxyphthalimideHCID 1029572-Methyl-3-pentyloxiraneHCID 5356796cis-2-Octene

Produkt 2

HCID 107231,2,3,4-Tetrahydro-1-naphthalenolAusbeute 34 %HCID 107241-TetraloneAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6277Cobalt diacetateKatalysatorHCID 98885Molybdenum carbonyl (Mo(CO)6)KatalysatorHCID 7505BenzonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A mixture of 4 mmol of cis-2-octene, 20 mmol of tetralin, 0.4 mmol of N-hydroxyphthalimide, 0.2 mmol of molybdenum hexacarbonyl, 0.004 mmol of cobalt (II) acetate, 200 mg of Molecular Sieve 4A, and 2 ml of benzonitrile was stirred at 50° C. under an oxygen atmosphere (1 atm) for 14 hours. Gas chromatographic analysis of products in a reaction mixture revealed that 2-octene was converted, at a rate of 83%, into 2,3-epoxyoctane (cis/trans=98.5/1.5) in yield of 72%, and that tetralin was converted, at a rate of 35%, into α-tetralol (yield: 34%) and α-tetralone (yield: 46%).

Quellen und Nachweise

ORD-Eintrag
ord-fe12c25a1fc04716950c0f2b37e7c761
Quelldatensatz
uspto-grants-2001_05
Patentnummer
US06229023B1

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