Reaktion #8997

Reaktionsgleichung

Terephthaldicarboxaldehyde

2-(aminomethyl)pyridine

hydrogen

→

title compound

Ausbeute 78.0%

4-hydroxymethylbenzaldehyde

Ausbeute 78.0%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe mixture was filtered through celite
2. 2
   Waschenthe cake washed with methanol
3. 3
   Sonstigethe solvent from the eluent removed in vacuo
4. 4
   SonstigePurification of the crude product by column chromatography on silica gel (EtOAc/Hexanes, 1:1)

Vorschrift

Terephthaldicarboxaldehyde (30.02 g, 224 mmol), methanol (200 mL), palladium on activated carbon, (10%, 3.02 g) and 2-(aminomethyl)pyridine (2.3 mL, 22 mol, 0.01 mol equiv) were combined in a hydrogenation vessel and the reaction mixture was shaken on a Parr hydrogenator for 2.5 hours at 40 psi of hydrogen. The mixture was filtered through celite, the cake washed with methanol and the solvent from the eluent removed in vacuo. Purification of the crude product by column chromatography on silica gel (EtOAc/Hexanes, 1:1) afforded the title compound (23.8 g, 78%) as a white solid. 1H NMR (CDCl3) δ 4.80 (s, 2H), 7.53 (d, 2H, J=9 Hz), 7.87 (d, 2H, J=9 Hz), 10.00 (s, 1H).

Quelle