تفاعل #421095

معادلة التفاعل

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

DIBAL-H

NH4Cl

→

3-(4-methoxy-phenyl)-propionaldehyde

المردود 70.7%

المذيبات

toluene

dry ice acetone

ظروف التفاعل

المعالجة

1. 1
   استخلاصThe solution was extracted twice with ether
2. 2
   غسيلthe organic layer was washed with brine
3. 3
   تجفيفdried over MgSO4(s)
4. 4
   تركيزconcentrated under reduced pressure
5. 5
   أخرىThe residue was purified by column chromatography on silica gel

الإجراء التجريبي

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.

المصدر