Methyl 2-((2,3-dimethylphenyl)amino)benzoate → 2-[(2,3-Dimethylphenyl)amino]benzenemethanol

HRID 1195873Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1195873
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH:19]=[CH:18][CH:17]=[CH:16][C:11]=1[C:12](OC)=[O:13].[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH:19]=[CH:18][CH:17]=[CH:16][C:11]=1[CH2:12][OH:13]

Komponenten

4

Edukt 2

HCID 71040Methyl 2-((2,3-dimethylphenyl)amino)benzoateHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 150273742-[(2,3-Dimethylphenyl)amino]benzenemethanolAusbeute 94,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

A solution of 2-[(2,3-dimethylphenyl) amino]benzoic acid, methyl ester (31 g, 121.5 mmol) in dry ether (600 ml) is added dropwise to a suspension of lithium aluminum hydride (6.9 g, 0.18 mmol) in dry ether (200 ml) under an atmosphere of dry nitrogen. The reaction mixture is stirred at room temperature overnight and quenched by the careful dropwise addition of water (7 ml), 15% NaOH (7 ml) and water (20 ml). The resulting suspension is filtered and the filtrate is evaporated to an oil which crystallizes upon addition of hexane to give pure 2-[(2,3-dimethylphenyl)amino]benzyl alcohol (26 g, 94%); mp 65°-69° C.

Aufarbeitung

  1. customquenched by the careful dropwise addition of water (7 ml), 15% NaOH (7 ml) and water (20 ml)
  2. filtrationThe resulting suspension is filtered
  3. customthe filtrate is evaporated to an oil which
  4. customcrystallizes upon addition of hexane

Quellen und Nachweise

ORD-Eintrag
ord-073499d8f7e34a348f7358873e932fb4
Quelldatensatz
uspto-grants-1992_05
Patentnummer
US05112846

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