Water → HCID 19885222, Verbindung

HRID 846252

Reaktionsgleichung

Reaktionsgleichung von HRID 846252
[CH2:1]([O:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=O)=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[F:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][C:24]#[N:25])=[CH:19][CH:18]=1.[OH-].[Na+].O>CO>[CH2:1]([O:7][C:8]1[CH:15]=[CH:14][C:11]([CH2:12][CH:23]([C:20]2[CH:21]=[CH:22][C:17]([F:16])=[CH:18][CH:19]=2)[CH2:24][NH2:25])=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Komponenten

6

Edukt 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 68016Benzeneacetonitrile, 4-fluoro-HCID 79816p-(Hexyloxy)benzaldehyde

Produkt 1

HCID 19885222HCID 19885222, VerbindungAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 51.5 g of 4-hexyloxybenzaldehyde and 33.8 g of 4-fluorophenylacetonitrile in methanol was stirred at room temperature and aqueous sodium hydroxide (50 percent) was added dropwise until a precipitate appeared. Water was then added and the solids were collected by filtration to render α-[[4-(hexyloxy)phenyl]methylene]-4-fluorophenylacetonitrile which was reduced as follows. 40.2 g of said nitrile, 10 g of Raney nickel, 150 ml of anhydrous ammonia and 300 ml of tetrahydrofuran were stirred at 110° for 12 hours at a pressure of 2000 psi. The catalyst and solvent were removed and the hydrochloride salt was made in the filtrate by the addition of anhydrous hydrochloric acid. Recrystallization from methanol rendered the title compound (20 percent yield).

Aufarbeitung

  1. filtrationthe solids were collected by filtration
  2. customThe catalyst and solvent were removed
  3. additionthe hydrochloride salt was made in the filtrate by the addition of anhydrous hydrochloric acid
  4. customRecrystallization from methanol

Quellen und Nachweise

ORD-Eintrag
ord-90628494bc12430485abf93a5704b848
Quelldatensatz
uspto-grants-1992_08
Patentnummer
US05135955

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