Methyl 3-amino-4-methylbenzoate → (3-Amino-4-methylphenyl)methanol

HRID 1090635

Reaktionsgleichung

Reaktionsgleichung von HRID 1090635
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH3:12])[C:5](OC)=[O:6].[BH4-].[Li+]>COCCOCCOC>[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH3:12])[CH2:5][OH:6]

Komponenten

4

Edukt 2

HCID 337778Methyl 3-amino-4-methylbenzoateHCID 4148881Lithium borohydride2×

Produkt 1

HCID 586243(3-Amino-4-methylphenyl)methanolAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8150DiglymeLösungsmittel

Versuchsvorschrift

Methyl 3-amino-4-methylbenzoate (16.52 g, 0.1 mol) was dissolved in diglyme (150 ml), lithium borohydride (2.18 g, 0.1 mol) added, and the solution stirred at room temperature overnight. A further portion of lithium borohydride (2.18 g, 0.1 mol) was added, and the mixture heated at reflux for 20 minutes. The reaction was quenched with water, the solvent evaporated, the residue dissolved in water, the solution adjusted to pH 5 with hydrochloric acid, and the product extracted into dichloromethane. Drying, evaporation and trituration with ether gave 3-amino-4-methylbenzyl alcohol (7.3 g, 54%), m.p. 105°-107°.

Aufarbeitung

  1. temperaturethe mixture heated
  2. temperatureat reflux for 20 minutes
  3. customThe reaction was quenched with water
  4. customthe solvent evaporated
  5. dissolutionthe residue dissolved in water
  6. extractionthe product extracted into dichloromethane
  7. customDrying
  8. customevaporation and trituration with ether

Quellen und Nachweise

ORD-Eintrag
ord-2876b2df4dc640f6a5c36e0b061b89c4
Quelldatensatz
uspto-grants-1992_01
Patentnummer
US05082848

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