Reaktion #63009

Reaktionsgleichung

NaH

methyl 4-hydroxybenzoate

Allyl bromide

hexane

→

title product

Methyl 4-(Allyloxy)benzoate

Lösungsmittel

ether

water

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONthe reaction mixture was poured into 400 ml
2. 2
   SonstigeThe layers were separated
3. 3
   Extraktionthe aqueous layer extracted 4×150 ml
4. 4
   Waschenwashed 2×150 ml
5. 5
   Trocknensaturated NaHCO3, dried over MgSO4

Vorschrift

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).

Quelle