Thionyl Chloride → 6-Methoxy-1-Indanone

Temperature

0 °C

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.

1. additionwas added slowly at 0° C
2. customthe solvent was removed in vacuo
3. dissolutionThe residue was dissolved in 1000 mL of methylene chloride
4. additionThe above mixture was poured onto ice
5. filtrationthe resulting mixture was filtered through celite
6. extractionthe aqueous layer was extracted with methylene chloride (2×200 mL)
7. dry with materialThe combined organic layer was dried over sodium sulfate
8. concentrationconcentrated in vacuo
9. extractionthe residue was extracted with hexane

ORD record

ord-ced77e34cc7e4cfb8becdf545d3ee0cd

Source dataset

uspto-grants-1997_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05631264