Réaction #58372

Équation de réaction

potassium carbonate

2-hydroxy-6-methoxybenzaldehyde

geranyl bromide

→

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

Solvants

DMF

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source