反応 #1253190

反応方程式

potassium carbonate

potassium iodide

vanillin

6-chlorohexanol

→

4-(6-hexyloxy)-3-methoxybenzaldehyde

収率 84.5%

溶媒

water

dimethyl sulphoxide

反応条件

後処理

1. 1
   温度The mixture is then cooled to room temperature
2. 2
   抽出extracted three times with 150 ml of ethyl acetate each time
3. 3
   洗浄The combined organic phases are washed twice with 200 ml of water each time
4. 4
   乾燥dried over magnesium sulphate
5. 5
   ろ過filtered
6. 6
   濃縮concentrated
7. 7
   その他Purification of the residue by chromatography on 400 g of silica gel

実験手順

41.45 g (300 mmol) of potassium carbonate and 27.4 g (165 mmol) of potassium iodide are added to a solution of 22.8 g (150 mmol) of vanillin and 30.7 g (225 mmol) of 6-chlorohexanol in 500 ml of dimethyl sulphoxide (DMSO) and the mixture is stirred overnight at 60° C. under nitiogen. The mixture is then cooled to room temperature, poured into 600 ml of water and extracted three times with 150 ml of ethyl acetate each time. The combined organic phases are washed twice with 200 ml of water each time, dried over magnesium sulphate, filtered and concentrated. Purification of the residue by chromatography on 400 g of silica gel using cyclohexane/ethyl acetate 1:1 yields 29.95 g of 4-(6-hexyloxy)-3-methoxybenzaldehyde.

出典