تفاعل #58372

معادلة التفاعل

potassium carbonate

2-hydroxy-6-methoxybenzaldehyde

geranyl bromide

→

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

المذيبات

DMF

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر