Reacción #953138

Ecuación de reacción

3-(4-methoxyphenyl)propionic acid

thionyl chloride

aluminum chloride

→

6-methoxy-1-indanone

Rendimiento 88.4%

Disolventes

methylene chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added slowly at 0° C
2. 2
   Otrothe 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
   Filtraciónthe resulting mixture was filtered through celite
6. 6
   Extracciónthe aqueous layer was extracted with methylene chloride (2×200 ml)
7. 7
   SecadoThe combined organic layer was dried over sodium sulfate
8. 8
   Concentraciónconcentrated in vacuo
9. 9
   Extracciónthe residue was extracted with hexane

Procedimiento

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.

Fuente