Reaktion #337684

Reaktionsgleichung

3-methyl-p-hydroxybenzaldehyde

ethylene glycol

p-toluenesulfonic acid

toluene

→

product

Ausbeute 24.0%

2-(2-hydroxyethoxy)-2-(4-hydroxy-3-methylphenyl)-1,3-dioxolane

Ausbeute 24.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated
2. 2
   Temperaturunder reflux
3. 3
   SonstigeThe toluene was removed in vacuo and saturated solution of sodium hydrogen carbonate (20 ml)
4. 4
   workup.ADDITIONwas added to the residue, which
5. 5
   Extraktionwas then extracted with ethyl acetate (3×20 ml)
6. 6
   WaschenThe organic layer was washed with water (20 ml)
7. 7
   Trocknendried over anhydrous sodium sulfate
8. 8
   Sonstigethe solvent was removed in vacuo
9. 9
   SonstigeThe residue was then recrystallised from an ethyl acetate and hexane mixture

Vorschrift

A mixture of 3-methyl-p-hydroxybenzaldehyde (0.5 g, 3.6 mmol), ethylene glycol (0.34 g, 5.5 mmol) and p-toluenesulfonic acid (0.07 g, 0.36 mmol) in toluene was heated under reflux. After 24 h, the reaction mixture was cooled to room temperature, TLC showed no starting material. The toluene was removed in vacuo and saturated solution of sodium hydrogen carbonate (20 ml) was added to the residue, which was then extracted with ethyl acetate (3×20 ml). The organic layer was washed with water (20 ml), dried over anhydrous sodium sulfate and the solvent was removed in vacuo. The residue was then recrystallised from an ethyl acetate and hexane mixture to give the product as a brown solid in 24% yield.

Quelle