Reaktion #2045100

Reaktionsgleichung

potassium tert-butylate

E-3-(4-methylphenyl)-2-methyl-2-propen-1-ol

allyl bromide

→

desired product

Ausbeute 95.0%

1-[(1E)-3-(Allyloxy)-2-methyl-1-propenyl]-4-methylbenzene

Ausbeute 95.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction was warmed up to room temperature overnight
2. 2
   workup.ADDITIONpoured onto water (800 ml)
3. 3
   ExtraktionThe reaction was extracted twice with ethyl acetate
4. 4
   WaschenEach organic phase was washed with water and brine
5. 5
   TrocknenCombined extracts were dried over solid anhydrous sodium sulfate
6. 6
   FiltrationThe solid was filtered off
7. 7
   Waschenrinsed with diethyl ether
8. 8
   Sonstigethe solvents were removed under vacuum
9. 9
   workup.DISTILLATIONThe product was purified by distillation under vacuum through a 20-cm Widmer column

Vorschrift

Solid potassium tert-butylate (47 g, 0.411 mol) was added portion-wise to a solution of E-3-(4-methylphenyl)-2-methyl-2-propen-1-ol (68.05 g, 0.420 mol) in dry THF (800 ml) at room temperature under nitrogen (exothermic to 30° C.). After 1 more hour at room temperature, the reaction was cooled to 5° C. and tetra butyl ammonium iodide (7.9 g, 0.021 mol) was added followed by allyl bromide (102.65 g, 0.840 mol) drop-wise. The reaction was warmed up to room temperature overnight and poured onto water (800 ml). The reaction was extracted twice with ethyl acetate. Each organic phase was washed with water and brine. Combined extracts were dried over solid anhydrous sodium sulfate. The solid was filtered off, rinsed with diethyl ether and the solvents were removed under vacuum. The product was purified by distillation under vacuum through a 20-cm Widmer column. 79 g of the desired product were obtained (yield=93%).

Quelle