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Acetonitrile → Pentanenitrile, 4,4-dimethyl-3-oxo-

HRID 568588
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 568588
[H-].[Na+].[C:3]([O:9]C)(=O)[C:4]([CH3:7])([CH3:6])[CH3:5].[C:11](#[N:13])[CH3:12].[H][H]>C1(C)C=CC=CC=1.O>[C:3]([CH2:12][C:11]#[N:13])(=[O:9])[C:4]([CH3:7])([CH3:6])[CH3:5]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 6342AcetonitrileHCID 24758Sodium hydrideHCID 69027Methyl pivalateHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel
HCID 1140
Toluene
Lösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

55 grams of sodium hydride (as an 80 weight % suspension in white oil) were suspended in 500 ml of dry toluene, 106 grams (0.914 mole) of methyl pivalate added and the mixture heated to 85° C. Then under vigorous stirring there was dropped in 77 grams (1.87 moles) of acetonitrile within 4 hours. Stirring was continued subsequently at 85° C. until the end of the development of hydrogen. The thickly liquid reaction mass was cooled to room temperature, treated with 700 ml of water, stirred vigorously for 30 minutes and the two phases separated in a separatory funnel. The aqueous phase was acidified with 31 weight % of hydrochloric acid at a pH 1-2 and 0° C. The precipitated pivaloylacetonitrile was filtered off with suction, washed until neutral with ice water and dried to constant weight at 25 Torr and 40° C. There were obtained 106 grams (93% of theory) of analytically pure pivaloylacetonitrile having a melting point of 65°-68° C.

Aufarbeitung

  1. stirringStirring
  2. customThe thickly liquid reaction mass
  3. temperaturewas cooled to room temperature
  4. stirringstirred vigorously for 30 minutes
  5. customthe two phases separated in a separatory funnel
  6. customwas acidified with 31 weight % of hydrochloric acid at a pH 1-2 and 0° C
  7. filtrationThe precipitated pivaloylacetonitrile was filtered off with suction
  8. washwashed until neutral with ice water
  9. customdried to constant weight at 25 Torr and 40° C

Quellen und Nachweise

ORD-Eintrag
ord-c2af4188fc7b4c41952e36a247b35139
Quelldatensatz
uspto-grants-1988_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04728743

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