Reaktion #59965

Reaktionsgleichung

benzyloxyacetaldehyde

ethylene glycol

p-toluenesulfonic acid monohydrate

sodium hydroxide

→

title compound

Ausbeute 77.5%

2-((benzyloxy)methyl)-1,3-dioxolane

Ausbeute 77.5%

Lösungsmittel

toluene

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGfurther stirred at 150° C. for 3 hours
2. 2
   TemperaturAfter cooled on ice
3. 3
   SonstigeAn organic layer was separated
4. 4
   Waschenwashed with water (three times)
5. 5
   TrocknenThe organic layer was dried over anhydrous sodium sulfate
6. 6
   Einengenconcentrated
7. 7
   SonstigeThe crude product was purified by silica gel column chromatography (NH silica gel, elution solvent: heptane/ethyl acetate=1/0 to 9/1 gradient)
8. 8
   EinengenDesired fractions were concentrated

Vorschrift

A mixture of benzyloxyacetaldehyde (3 g, 20 mmol), ethylene glycol (1.23 ml, 22 mmol), p-toluenesulfonic acid monohydrate (344 mg, 1.8 mmol), and toluene (15 ml) was stirred at 140° C. for 2 hours and further stirred at 150° C. for 3 hours. After cooled on ice, a 2N aqueous sodium hydroxide solution and ethyl acetate were added to the reaction mixture. An organic layer was separated, washed with water (three times) and a saturated saline solution. The organic layer was dried over anhydrous sodium sulfate and concentrated. The crude product was purified by silica gel column chromatography (NH silica gel, elution solvent: heptane/ethyl acetate=1/0 to 9/1 gradient). Desired fractions were concentrated to obtain the title compound (3.01 g, 77.5% yield) as a light yellow oil.

Quelle