반응 #63009

반응 방정식

NaH

methyl 4-hydroxybenzoate

Allyl bromide

hexane

→

title product

Methyl 4-(Allyloxy)benzoate

용매

ether

water

DMF

반응 조건

후처리

1. 1
   workup.ADDITIONthe reaction mixture was poured into 400 ml
2. 2
   기타The layers were separated
3. 3
   추출the aqueous layer extracted 4×150 ml
4. 4
   세척washed 2×150 ml
5. 5
   건조saturated NaHCO3, dried over MgSO4

실험 절차

NaH (60% in oil, 10 g., 0.25 mol) was washed 3×100 ml. hexane in place. 350 ml. DMF was then added, the mixture stirred under N2, and methyl 4-hydroxybenzoate (38.0 g., 0.25 mol) added portionwise over 20 minutes as H2 evolved. Allyl bromide (21.6 ml., 0.25 mol) was then added via syringe over 5 minutes. After 40 minutes additional stirring, the reaction mixture was poured into 400 ml. ice and water and 150 ml. ether was added. The layers were separated and the aqueous layer extracted 4×150 ml. fresh ether and 1×100 ml. hexane. The organic layers were combined, washed 2×150 ml. saturated NaHCO3, dried over MgSO4, and stripped to yield title product, 47.6 g., 3.89 (s, 3H), 4.60 (m, 2H), 5.46 (m, 2H), 6.1 (m, 1H), 6.99 (d, 2 H), 8.10 (d, 2H).

출처