Réaction #4822

Équation de réaction

p-hydroxyacetophenone

1-bromo-3-chloropropane

potassium hydroxide

→

p-chloropropoxy acetophenone

Rendement 68.0%

Solvants

methanol

Conditions de réaction

Traitement

1. 1
   Températureat reflux for 24 hours
2. 2
   Filtrationfiltered through Celite
3. 3
   Autreevaporated in vacuo
4. 4
   workup.ADDITIONThe residual semi-solid was diluted with diethyl ether (500 ml)
5. 5
   Lavagewashed with H2O (2×300 ml)
6. 6
   SéchageThe ether solution was dried over MgSO4
7. 7
   Filtrationfiltered
8. 8
   Autreevaporated in vacuo

Mode opératoire

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).

Source