Reacción #4822

Ecuación de reacción

p-hydroxyacetophenone

1-bromo-3-chloropropane

potassium hydroxide

→

p-chloropropoxy acetophenone

Rendimiento 68.0%

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaat reflux for 24 hours
2. 2
   Filtraciónfiltered through Celite
3. 3
   Otroevaporated in vacuo
4. 4
   workup.ADDITIONThe residual semi-solid was diluted with diethyl ether (500 ml)
5. 5
   Lavadowashed with H2O (2×300 ml)
6. 6
   SecadoThe ether solution was dried over MgSO4
7. 7
   Filtraciónfiltered
8. 8
   Otroevaporated in vacuo

Procedimiento

To a mixture of p-hydroxyacetophenone (50.7 g, 0.37 mol) and 1-bromo-3-chloropropane (160 ml, 1.5 mol) in methanol (250 ml) was added portionwise potassium hydroxide (63 g, 1.12 mol). The mixture was stirred at reflux for 24 hours, cooled to room temperature, filtered through Celite and evaporated in vacuo. The residual semi-solid was diluted with diethyl ether (500 ml) and washed with H2O (2×300 ml). The ether solution was dried over MgSO4, filtered and evaporated in vacuo to give p-chloropropoxy acetophenone as a liquid in 68% yield (53.38 g). 1H NMR (CDCl3): δ7.98-7.89 (d, J=8.9 Hz, 2H), 7.02-6.92 (d, J=8.9 Hz, 2H), 4.16 (t, J=5.9 Hz, 2H), 3.75 (t, J=6.4 Hz, 2H), 2.52 (s, 3H), 2.34-2.16 (m, 2H).

Fuente