반응 #50466

반응 방정식

crude product

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

→

yellow oily solid

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

용매

thionyl chloride

반응 조건

후처리

1. 1
   온도heated
2. 2
   온도at reflux for 2 hours
3. 3
   기타Thionyl chloride was removed by concentration at reduced pressure
4. 4
   농축the 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
   추출extracted three times with ether
8. 8
   기타chromatographed on silica gel (10% ethyl acetate/hexane)

실험 절차

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) .

출처