Reaktion #50466

Reaktionsgleichung

crude product

3-chloro-α-(4-chlorophenyl)benzenepropanoic acid

→

yellow oily solid

5-chloro-2-(4-chlorophenyl)-2,3-dihydro-1H-inden-1-one

Lösungsmittel

thionyl chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturheated
2. 2
   Temperaturat reflux for 2 hours
3. 3
   SonstigeThionyl chloride was removed by concentration at reduced pressure
4. 4
   Einengenthe mixture was concentrated several times from carbon tetrachloride
5. 5
   workup.ADDITION24.5 g of aluminum trichloride was then added
6. 6
   workup.ADDITIONwas poured onto a mixture of ice in 1N hydrochloric acid
7. 7
   Extraktionextracted three times with ether
8. 8
   Sonstigechromatographed on silica gel (10% ethyl acetate/hexane)

Vorschrift

The crude product from Step A was combined with 50 ml of thionyl chloride and then heated at reflux for 2 hours. Thionyl chloride was removed by concentration at reduced pressure and then the mixture was concentrated several times from carbon tetrachloride. The residue was combined with 200 ml of dichloroethane, cooled under nitrogen to 0° C., and 24.5 g of aluminum trichloride was then added. After stirring overnight the reaction was poured onto a mixture of ice in 1N hydrochloric acid, extracted three times with ether and chromatographed on silica gel (10% ethyl acetate/hexane) to afford 18.6 g of a yellow oily solid. 1H NMR (CDCl3) δ 3.20 (dd, 1H), 3.68 (dd, 1H), 3.90 (dd, 1H), 6.9-7.6 (m), 7.75 (d, 1H) .

Quelle