Reaktion #4822

Reaktionsgleichung

p-hydroxyacetophenone

1-bromo-3-chloropropane

potassium hydroxide

→

p-chloropropoxy acetophenone

Ausbeute 68.0%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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).

Quelle