3-(3,4-Dichlorophenyl)propionic acid → 5,6-Dichloro-2,3-dihydro-1H-inden-1-one

Temperature

50 °C

A mixture of 20 g of 3-(3,4-dichlorophenyl)-propionic acid [J. Med. Chem., Vol. 16(2) (1973), p. 101-106 ] and 100 ml of thionyl chloride was refluxed for 30 minutes and the thionyl chloride was then evaporated. The residue was taken up in 20 ml of methylene chloride and the solution was poured into a suspension of 20 g of aluminum chloride in 150 ml of methylene chloride. The mixture was stirred for one hour at room temperature and 30 minutes at 50° C. The mixture was poured over ice and was stirred for 30 minutes and then was extracted with methylene chloride. The organic phase was washed with water, dried and evaporated to dryness and the residue was taken up in ether and vacuum filtered. The product was dried to obtain 80 g of the desired product melting at 155° C.

1. temperaturewas refluxed for 30 minutes
2. customthe thionyl chloride was then evaporated
3. additionthe solution was poured into a suspension of 20 g of aluminum chloride in 150 ml of methylene chloride
4. additionThe mixture was poured over ice
5. stirringwas stirred for 30 minutes
6. extractionwas extracted with methylene chloride
7. washThe organic phase was washed with water
8. customdried
9. customevaporated to dryness
10. filtrationvacuum filtered
11. customThe product was dried

ORD record

ord-aba34b4fd8fd4a46aa8e09c10bf0478f

Source dataset

uspto-grants-1994_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05348971