Reacción #337684

Ecuación de reacción

3-methyl-p-hydroxybenzaldehyde

ethylene glycol

p-toluenesulfonic acid

toluene

→

product

Rendimiento 24.0%

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

Rendimiento 24.0%

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas heated
2. 2
   Temperaturaunder reflux
3. 3
   OtroThe 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
   Extracciónwas then extracted with ethyl acetate (3×20 ml)
6. 6
   LavadoThe organic layer was washed with water (20 ml)
7. 7
   Secadodried over anhydrous sodium sulfate
8. 8
   Otrothe solvent was removed in vacuo
9. 9
   OtroThe residue was then recrystallised from an ethyl acetate and hexane mixture

Procedimiento

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.

Fuente