반응 #1880959

반응 방정식

hydrochloric acid

5,6-dimethoxy-3-methylindan-1-one

hydrochloric acid

→

5,6-dimethoxy-1-methylindane

수율 75.0%

용매

water

water

toluene

반응 조건

후처리

1. 1
   기타The supernatant was decanted off
2. 2
   workup.ADDITIONto the residue were added, with ice cooling, 42 ml of water
3. 3
   workup.ADDITIONwere added
4. 4
   온도the mixture was refluxed for 3 days (d)
5. 5
   workup.WAITin the course of which, after 48 h
6. 6
   온도After cooling
7. 7
   추출the product was extracted twice in 300 ml of ether
8. 8
   세척The combined extracts were washed with 100 ml of water and 25 ml of saturated sodium chloride solution
9. 9
   건조dried over sodium sulfate
10. 10
    농축concentrated on a rotary evaporator

실험 절차

To a suspension of 53.3 g (815 mmol) of zinc dust in 74 ml of water were added 4 ml of concentrated hydrochloric acid. The supernatant was decanted off after stirring for 30 min, and to the residue were added, with ice cooling, 42 ml of water and then, dropwise, 55 ml of concentrated hydrochloric acid. 28.0 g (136 mmol) of 5,6-dimethoxy-3-methylindan-1-one dissolved in 53 ml of toluene were added and the mixture was refluxed for 3 days (d), in the course of which, after 48 h, a further 55 ml of concentrated hydrochloric acid were added. After cooling, the reaction mixture was poured into 200 ml of water and the product was extracted twice in 300 ml of ether. The combined extracts were washed with 100 ml of water and 25 ml of saturated sodium chloride solution, dried over sodium sulfate and concentrated on a rotary evaporator. After flash chromatography (pentane/ether, 9:1, Rf=0.23) on silica gel, 19.6 g (75%) of 5,6-dimethoxy-1-methylindane were obtained.

출처