Acetone → HCID 11118528, Verbindung

HRID 1756744Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1756744
[CH3:1][C:2]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][C:3]=1[O:4][CH2:5][C:6]1[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=1[CH2:8]Cl.[C-:19]#[N:20].[Na+].CC(C)=O>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.O>[CH3:1][C:2]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][C:3]=1[O:4][CH2:5][C:6]1[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=1[CH2:8][C:19]#[N:20]

Komponenten

6

Edukt 3

HCID 180AcetoneHCID 8929Sodium CyanideHCID 10879843HCID 10879843, Verbindung

Produkt 1

HCID 11118528HCID 11118528, VerbindungAusbeute 97,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 66133Benzyl triethylammonium chlorideKatalysatorHCID 962WaterLösungsmittel2×

Versuchsvorschrift

2-(2,5-Dimethylphenoxymethyl)benzyl chloride (Purity: 86.8%, 1.50 g, 5 mmol), 95% sodium cyanide (0.31 g, 6 mmol), triethylbenzylammonium chloride (0.06 g, 0.25 mmol), acetone (4 ml) and water (2 ml) were added. The mixture was heated under reflux for 5 hours. After completion of the reaction, water (100 ml) was added. The resulting mixture was extracted with ether (100 ml), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (ethyl acetate/n-hexane) to give 2-(2,5-dimethylphenoxymethyl)benzyl cyanide (1.23 g, Yield: 97.8%).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 5 hours
  3. additionwas added
  4. extractionThe resulting mixture was extracted with ether (100 ml)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel chromatography (ethyl acetate/n-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-ece814a5ade64485aab6f64bfc021c3f
Quelldatensatz
uspto-grants-1995_08
Patentnummer
US05442063

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