Reaktion #953138

Reaktionsgleichung

3-(4-methoxyphenyl)propionic acid

thionyl chloride

aluminum chloride

→

6-methoxy-1-indanone

Ausbeute 88.4%

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 sitrred 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