Reaktion #829624

Reaktionsgleichung

3-(4-methoxyphenyl)propionic acid

thionyl chloride

aluminum chloride

→

6-methoxy-1-indanone

Ausbeute 88.0%

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added slowly at 0° C
2. 2
   Sonstigethe solvent was removed in vacuo
3. 3
   workup.DISSOLUTIONThe residue was dissolved in 1000 mL of methylene chloride
4. 4
   workup.ADDITIONThe above mixture was poured onto ice
5. 5
   Filtrationthe resulting mixture was filtered through celite
6. 6
   Extraktionthe aqueous layer was extracted with methylene chloride (2×200 mL)
7. 7
   TrocknenThe combined organic layer was dried over sodium sulfate
8. 8
   Einengenconcentrated in vacuo
9. 9
   Extraktionthe residue was extracted with hexane

Vorschrift

To a solution of 3-(4-methoxyphenyl)propionic acid (50.34 g, 0,279 mol) in 500 mL of methylene chloride cooled to 0° C. was added slowly at 0° C. 30.5 mL (0.418 mol) of thionyl chloride, the mixture was stirred 10 h at room temperature and the solvent was removed in vacuo. The residue was dissolved in 1000 mL of methylene chloride, cooled to 0° C., and 40.92 g (0.306 mol) of aluminum chloride was added in small portions and the resulting mixture was stirred at room temperature for 1 h. The above mixture was poured onto ice, the resulting mixture was filtered through celite, and the aqueous layer was extracted with methylene chloride (2×200 mL). The combined organic layer was dried over sodium sulfate, concentrated in vacuo, and the residue was extracted with hexane to afford 40 g (88%) of 6-methoxy-1-indanone.

Quelle