Reaction #4822

Reaction equation

p-hydroxyacetophenone

1-bromo-3-chloropropane

potassium hydroxide

→

p-chloropropoxy acetophenone

Yield 68.0%

Solvents

methanol

Conditions

Workup

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

Procedure

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