تفاعل #337685

معادلة التفاعل

p-hydroxybenzaldehyde

ethylene glycol

pyridinium toluene sulphonate

p-toluene sulphonic acid monohydrate

sodium bicarbonate

→

title compound

المردود 86.9%

2-(2-hydroxyethoxy)-2-(4-hydroxyphenyl)-1,3-dioxolane

المردود 86.9%

المذيبات

toluene

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe solution was refluxed overnight
2. 2
   تركيزbefore concentrating the solvent
3. 3
   أخرىto furnish an amber gum
4. 4
   استخلاصextracted with ethyl acetate (3×50 mL)
5. 5
   تجفيفThe organic extracts were dried over magnesium sulphate
6. 6
   ترشيحfiltered
7. 7
   تركيزconcentrated
8. 8
   أخرىto furnish a dark brown gum
9. 9
   أخرىThe gum was chromatographed on silica (ether/methanol, 9.5:0.5)

الإجراء التجريبي

To a solution of p-hydroxybenzaldehyde (1 g, 8.18 mmol) in anhydrous toluene (100 mL) was added ethylene glycol (0.68 mL, 12.28 mmol), pyridinium toluene sulphonate (0.2 g, 0.88 mmol) and p-toluene sulphonic acid monohydrate (0.16 g, 0.88 mmol). The solution was refluxed overnight before concentrating the solvent to furnish an amber gum. Saturated sodium bicarbonate (50 mL) was then added to the reaction mixture, and extracted with ethyl acetate (3×50 mL). The organic extracts were dried over magnesium sulphate, filtered, and concentrated to furnish a dark brown gum. The gum was chromatographed on silica (ether/methanol, 9.5:0.5) to furnish the title compound as a dark brown solid (173 mg, 9%).

المصدر