Methanol → Methyl 5-cyanopentanoate

HRID 1439536

Reaktionsgleichung

Reaktionsgleichung von HRID 1439536
[C:1](#[N:6])[CH2:2][CH:3]=[CH:4][CH3:5].N1C=CC=CC=1.C[OH:14].[O:15]1[CH2:19]CC[CH2:16]1>[C]=O.[CH-]=O.[CH-]=O.[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Co].[Co+2]>[CH3:16][O:15][C:19](=[O:14])[CH2:5][CH2:4][CH2:3][CH2:2][C:1]#[N:6]

Komponenten

7

Edukt 4

HCID 887MethanolHCID 1049PyridineHCID 8028TetrahydrofuranHCID 207503-Pentenenitrile, Pract.

Produkt 1

HCID 554130Methyl 5-cyanopentanoateAusbeute 70,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 25049Dicobalt Octacarbonyl (stabilized with 1-5% Hexane)KatalysatorHCID 178418416HCID 178418416, VerbindungLösungsmittel2×

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

An argon-filled shaking autoclave is charged with a mixture of 8.1 parts of 3-pentenonitrile, 1.4 parts of dicobalt octacarbonyl, 2.6 parts of pyridine, 8 parts of methanol and 30 parts of tetrahydrofuran. The pressure is brought to 140 bars by forcing in carbon monoxide at room temperature. The autoclave is next heated to 160° C; the pressure is then brought to 200 bars by forcing in carbon monoxide, and the reaction mixture is shaken for 4 hours under these conditions. After cooling, and letting down the pressure, the mixture is filtered. Fractional distillation of the reaction mixture gives 9.9 parts of 5-cyanovaleric acid methyl ester (70.1% of theory). Boiling point 118°-120° C/10 mm Hg, nD20 = 1.4322.

Aufarbeitung

  1. additionAn argon-filled
  2. stirringthe reaction mixture is shaken for 4 hours under these conditions
  3. temperatureAfter cooling
  4. filtrationthe mixture is filtered
  5. distillationFractional distillation of the reaction mixture

Quellen und Nachweise

ORD-Eintrag
ord-7ec56ffe3dbc44b682a7313dd9ccf11e
Quelldatensatz
uspto-grants-1977_11
Patentnummer
US04060543

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