Water → 6-Phenylhexanenitrile

HRID 440946Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 440946
CS(O[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=O)=O.[C-:17]#[N:18].[Na+].O>CN(C)C=O>[C:11]1([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][C:17]#[N:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 8929Sodium CyanideHCID 116301071-Methylsulfonyloxy-5-phenylpentane

Produkt 1

HCID 104647826-PhenylhexanenitrileAusbeute 949,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A stirred solution of 15.0 grams (0.0062 mole) of 1-methylsulfonyloxy-5-phenylpentane and 9.1 grams (0.190 mole) of sodium cyanide in 150 mL of N,N-dimethylformamide was heated at 50° C. to 55° C. for about 60 hours. After this time the reaction mixture was poured into 400 mL of water. The mixture was extracted with three 250 mL portions of diethyl ether. The combined extracts were then washed with three 200 mL portions of water and 200 mL of an aqueous solution saturated with sodium chloride. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, yielding 10.2 grams of 6-phenylhexanenitrile. The NMR spectrum was consistent with the proposed structure.

Aufarbeitung

  1. extractionThe mixture was extracted with three 250 mL portions of diethyl ether
  2. washThe combined extracts were then washed with three 200 mL portions of water and 200 mL of an aqueous solution saturated with sodium chloride
  3. dry with materialThe organic layer was dried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f79dbd5a05f64c40838cd993c3b0f486
Quelldatensatz
uspto-grants-1996_05
Patentnummer
US05521192

Notizen zur Reaktion

Wird geladen…