반응 #58372

반응 방정식

potassium carbonate

2-hydroxy-6-methoxybenzaldehyde

geranyl bromide

→

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

용매

DMF

반응 조건

후처리

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

실험 절차

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.

출처