2-[(2,3-Dimethylphenyl)amino]benzenemethanol → HCID 15027376, Verbindung

HRID 1461427Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1461427
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[CH3:12][C:13]1[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][C:14]=1[NH:20][C:21]1[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=1[CH2:23][OH:24]>ClCCl>[CH3:12][C:13]1[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][C:14]=1[NH:20][C:21]1[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=1[CH:23]=[O:24]

Komponenten

4

Edukt 2

HCID 150273742-[(2,3-Dimethylphenyl)amino]benzenemethanolHCID 178418287HCID 178418287, Verbindung

Produkt 1

HCID 15027376HCID 15027376, VerbindungAusbeute 48,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A suspension of pyridinium chlorochromate (47.5 g, 0.22 mol) and neutral alumina (170 g) in dichloromethane (600 ml) is stirred for 30 minutes at room temperature. 2-[(2,3-dimethylphenyl) amino]benzyl alcohol (25 g, 0.11 mol) is added and the reaction mixture is stirred at room temperature overnight. The suspension is filtered through a pad of silica gel (1000 g) and the product is eluted with dichloromethane (2500 ml). The combined filtrate and eluant are evaporated and the residue is recrystallized from cold methanol/water to give 2-[(2,3-dimethylphenyl)amino] benzaldehyde (11.95 g, 48%). Recrystallization from hexane at 0° C. gives analytical material; mp 45-47° C.

Aufarbeitung

  1. stirringthe reaction mixture is stirred at room temperature overnight
  2. filtrationThe suspension is filtered through a pad of silica gel (1000 g)
  3. washthe product is eluted with dichloromethane (2500 ml)
  4. customThe combined filtrate and eluant are evaporated
  5. customthe residue is recrystallized from cold methanol/water

Quellen und Nachweise

ORD-Eintrag
ord-5a4498bd823b499c82f381f7e24cce22
Quelldatensatz
uspto-grants-1991_12
Patentnummer
US05075330

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