반응 #337684

반응 방정식

3-methyl-p-hydroxybenzaldehyde

ethylene glycol

p-toluenesulfonic acid

toluene

→

product

수율 24.0%

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

수율 24.0%

반응 조건

후처리

1. 1
   온도was heated
2. 2
   온도under reflux
3. 3
   기타The 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
   추출was then extracted with ethyl acetate (3×20 ml)
6. 6
   세척The organic layer was washed with water (20 ml)
7. 7
   건조dried over anhydrous sodium sulfate
8. 8
   기타the solvent was removed in vacuo
9. 9
   기타The residue was then recrystallised from an ethyl acetate and hexane mixture

실험 절차

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.

출처