Reaktion #421095

Reaktionsgleichung

3-(4-Methoxy-phenyl)-propionic acid

DIBAL-H

NH4Cl

→

3-(4-methoxy-phenyl)-propionaldehyde

Ausbeute 70.7%

Lösungsmittel

toluene

dry ice acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   ExtraktionThe solution was extracted twice with ether
2. 2
   Waschenthe organic layer was washed with brine
3. 3
   Trocknendried over MgSO4(s)
4. 4
   Einengenconcentrated under reduced pressure
5. 5
   SonstigeThe residue was purified by column chromatography on silica gel

Vorschrift

3-(4-Methoxy-phenyl)-propionic acid (9a, 1.80 g, 10.0 mmol) in toluene (25.0 mL) was cooled to −78° C. in dry ice-acetone bath for 5-10 minutes under N2. DIBAL-H (11.0 mmol) was slowly added by syringe and stirred for 2 hours at −78° C. Then, the reaction mixture was poured quickly into an aqueous NH4Cl solution with vigorous stirring. The solution was extracted twice with ether and the organic layer was washed with brine, dried over MgSO4(s), and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to provide 3-(4-methoxy-phenyl)-propionaldehyde (9b, 1.16 g, 7.07 mmol) as yellow oil in 70.7% yield.

Quelle