반응 #4822

반응 방정식

p-hydroxyacetophenone

1-bromo-3-chloropropane

potassium hydroxide

→

p-chloropropoxy acetophenone

수율 68.0%

용매

methanol

반응 조건

후처리

1. 1
   온도at reflux for 24 hours
2. 2
   여과filtered through Celite
3. 3
   기타evaporated in vacuo
4. 4
   workup.ADDITIONThe residual semi-solid was diluted with diethyl ether (500 ml)
5. 5
   세척washed with H2O (2×300 ml)
6. 6
   건조The ether solution was dried over MgSO4
7. 7
   여과filtered
8. 8
   기타evaporated in vacuo

실험 절차

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).

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