Réaction #502078

Équation de réaction

sodium carbonate

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

acetic acid

tetrahydrofuran

→

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

Rendement 26.0%

Solvants

water

Conditions de réaction

Traitement

1. 1
   Autrefitted with thermocouple, magnetic stirrer and condenser
2. 2
   TempératureThe reaction mixture was refluxed for 2 hrs
3. 3
   Températurecooled
4. 4
   AutreThe crude reaction mixture
5. 5
   Extractionwas extracted with hexane (4×100 mL)
6. 6
   Séchagethe combined organic phase dried over magnesium sulphate
7. 7
   Filtrationfiltered
8. 8
   Autrethe solvent removed in vacuo
9. 9
   AutreThe crude product was chromatographed over silica gel (hexane/methyltert-butyl ether)

Mode opératoire

{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%).

Source