Terephthalaldehyde → 4-(Hydroxymethyl)benzaldehyde

HRID 7179

Reaktionsgleichung

Reaktionsgleichung von HRID 7179
[CH:1]1[C:6]([CH:7]=[O:8])=[CH:5][CH:4]=[C:3]([CH:9]=[O:10])[CH:2]=1.NCC1C=CC=CN=1.[H][H]>[Pd].CO>[OH:10][CH2:9][C:3]1[CH:2]=[CH:1][C:6]([CH:7]=[O:8])=[CH:5][CH:4]=1

Komponenten

6

Edukt 3

HCID 12173TerephthalaldehydeHCID 195092-PyridinemethanamineHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 5563304-(Hydroxymethyl)benzaldehydeAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

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) □ 4.80 (s, 2H), 7.53 (d, 2H, J=9 Hz), 7.87 (d, 2H, J=9 Hz), 10.00 (s, 1H).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-6cf759bc757143e7bba62c72bc8bb078
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07084155B2

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