Reacción #2045100

Ecuación de reacción

potassium tert-butylate

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

allyl bromide

→

desired product

Rendimiento 95.0%

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

Rendimiento 95.0%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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%).

Fuente