反応 #502078

反応方程式

sodium carbonate

{4-[(1,5-dimethylhexyl)oxy]butyl}-1,3-dioxolane

acetic acid

tetrahydrofuran

→

5-[(1,5-dimethylhexyl)oxy]pentanal

収率 26.0%

溶媒

water

反応条件

後処理

1. 1
   その他fitted with thermocouple, magnetic stirrer and condenser
2. 2
   温度The reaction mixture was refluxed for 2 hrs
3. 3
   温度cooled
4. 4
   その他The crude reaction mixture
5. 5
   抽出was extracted with hexane (4×100 mL)
6. 6
   乾燥the combined organic phase dried over magnesium sulphate
7. 7
   ろ過filtered
8. 8
   その他the solvent removed in vacuo
9. 9
   その他The crude product was chromatographed over silica gel (hexane/methyltert-butyl ether)

実験手順

{4-[(1,5-dimethylhexyl)oxy]butyl}-1,3-dioxolane (1.4 g, 43% pure by GC RPA, 3.9 mmol), acetic acid (10 mL), tetrahydrofuran (16 mL) and water (20 mL) were added to a 100 mL three-necked flask fitted with thermocouple, magnetic stirrer and condenser. The reaction mixture was refluxed for 2 hrs, cooled and saturated sodium carbonate (150 mL) added. The crude reaction mixture was extracted with hexane (4×100 mL), the combined organic phase dried over magnesium sulphate, filtered and the solvent removed in vacuo. The crude product was chromatographed over silica gel (hexane/methyltert-butyl ether) to yield pure 5-[(1,5-dimethylhexyl)oxy]pentanal as a colourless oil (0.22 g, 1.02 mmol, chemical yield 26%).

出典