反应详情

A mixture of 1-[4-hydroxy-3-(methylmercapto)phenyl]-ethanone (5.4 g; 30 mmol), K2CO3 (4.2 g), 1,3-dibromopropane (8 g, 39 mmol) in acetonitrile (150 ml) was heated at reflux for 3 hours and stirred at room temperature overnight. Acetonitrile was removed at reduced pressure and the residue was extracted into dichloromethane (250 ml). Insolubles were filtered off. The dichloromethane solution was concentrated. The crude product was purified on a silica gel column (SiO2, 100 g; eluted with 3:2 hexane:dichloromethane, 1.6 l). The compound crystallized upon concentration, and the product (3.5 g, 39%) was recrystallized from ethanol (40 ml) to yield 1-[4-(3-bromopropoxy)-3-(methylmercapto)phenyl]ethanone as white needles, 2.0 g;m.p.=120°-122° C.

1. temperaturewas heated
2. temperatureat reflux for 3 hours
3. customAcetonitrile was removed at reduced pressure
4. extractionthe residue was extracted into dichloromethane (250 ml)
5. filtrationInsolubles were filtered off
6. concentrationThe dichloromethane solution was concentrated
7. customThe crude product was purified on a silica gel column (SiO2, 100 g; eluted with 3:2 hexane:dichloromethane, 1.6 l)
8. customThe compound crystallized upon concentration
9. customthe product (3.5 g, 39%) was recrystallized from ethanol (40 ml)