Reacción #421095

Ecuación de reacción

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

DIBAL-H

NH4Cl

→

3-(4-methoxy-phenyl)-propionaldehyde

Rendimiento 70.7%

Disolventes

toluene

dry ice acetone

Condiciones de reacción

Tratamiento posterior

1. 1
   ExtracciónThe solution was extracted twice with ether
2. 2
   Lavadothe organic layer was washed with brine
3. 3
   Secadodried over MgSO4(s)
4. 4
   Concentraciónconcentrated under reduced pressure
5. 5
   OtroThe residue was purified by column chromatography on silica gel

Procedimiento

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.

Fuente