تفاعل #50466

معادلة التفاعل

crude product

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

→

yellow oily solid

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

المذيبات

thionyl chloride

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةheated
2. 2
   درجة الحرارةat reflux for 2 hours
3. 3
   أخرىThionyl chloride was removed by concentration at reduced pressure
4. 4
   تركيزthe 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
   استخلاصextracted three times with ether
8. 8
   أخرىchromatographed on silica gel (10% ethyl acetate/hexane)

الإجراء التجريبي

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) .

المصدر