Reacción #58372

Ecuación de reacción

potassium carbonate

2-hydroxy-6-methoxybenzaldehyde

geranyl bromide

→

2-((E)-3,7-dimethylocta-2,6-dienyloxy)-6-methoxybenzaldehyde

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   FiltraciónThe suspension was filtered through a layer of dry sodium sulfate (top) and silica gel (bottom)
2. 2
   Lavadowashed with 200 ml ethyl acetate
3. 3
   Otrodecanted into a separatory funnel
4. 4
   LavadoThe mixture was washed sequentially with aqueous ammonium chloride, water (twice), brine
5. 5
   Secadothe organic phase was dried over Na2SO4
6. 6
   ConcentraciónThe solution was concentrated in vacuo on a rotovap
7. 7
   OtroThe brown gel material was then purified by chromatography via silica gel using 8:2 hexanes

Procedimiento

To a solution of 2-hydroxy-6-methoxybenzaldehyde (4.72 g, 30.43 mmol) in dry DMF (50 ml) was added geranyl bromide (7.5 g, 33.50 mmol) followed by solid potassium carbonate (5.5 g, 39.86 mmol). The mixture was stirred at room temperature for 48 h. The suspension was filtered through a layer of dry sodium sulfate (top) and silica gel (bottom), washed with 200 ml ethyl acetate and decanted into a separatory funnel. The mixture was washed sequentially with aqueous ammonium chloride, water (twice), brine, and the organic phase was dried over Na2SO4. The solution was concentrated in vacuo on a rotovap. The brown gel material was then purified by chromatography via silica gel using 8:2 hexanes:ethyl acetate eluent to provide 2-((E)-3,7-dimethylocta-2,6-dienyloxy)-6-methoxybenzaldehyde as pale yellow oil.

Fuente