反応 #337684

反応方程式

3-methyl-p-hydroxybenzaldehyde

ethylene glycol

p-toluenesulfonic acid

toluene

→

product

収率 24.0%

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

収率 24.0%

反応条件

後処理

1. 1
   温度was heated
2. 2
   温度under reflux
3. 3
   その他The 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
   抽出was then extracted with ethyl acetate (3×20 ml)
6. 6
   洗浄The organic layer was washed with water (20 ml)
7. 7
   乾燥dried over anhydrous sodium sulfate
8. 8
   その他the solvent was removed in vacuo
9. 9
   その他The residue was then recrystallised from an ethyl acetate and hexane mixture

実験手順

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.

出典