Reaction #502078

Reaction equation

sodium carbonate

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

acetic acid

tetrahydrofuran

→

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

Yield 26.0%

Solvents

water

Conditions

Workup

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

Procedure

{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