3-Methyl-4-nitrobenzyl alcohol → (4-amino-3-methylphenyl)methanol

HRID 1634174Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1634174
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-])=O)[CH2:5][OH:6]>C(O)C.[Pd]>[OH:6][CH2:5][C:4]1[CH:7]=[CH:8][C:9]([NH2:10])=[C:2]([CH3:1])[CH:3]=1

Komponenten

4

Edukt 1

HCID 5913603-Methyl-4-nitrobenzyl alcohol2×

Produkt 1

HCID 1514189(4-amino-3-methylphenyl)methanolAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 3-methyl-4-nitrobenzyl alcohol (compound 12-1, 8.5 g, 50.9 mmol) in ethanol (100 mL) was stirred at room temperature, while 10% Pd/C (1.0 g) was added in one portion. The resulting suspension was hydrogenated (10 psi) in a Parr apparatus at room temperature for 1.5 hours. The catalyst was removed by filtration, and solvent was evaporated under vacuum to give the title compound (12-2, 6.9 g, 99%). MS (electrospray) 138 (M+1); 1H N MR (CDCl3) δ2.16 (s, 3H), 2.72 (br s, 3H), 4.52 (s, 2H), 6.64 (d, 1H, J=8.0 Hz), 7.02 (d, 1H, J=8.0 Hz), 7.05 (s, 1H).

Aufarbeitung

  1. additionwas added in one portion
  2. customat room temperature
  3. customfor 1.5 hours
  4. customThe catalyst was removed by filtration, and solvent
  5. customwas evaporated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-08e5402405914c638635ef6500887810
Quelldatensatz
uspto-grants-2003_01
Patentnummer
US06506761B1

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