반응 #59965

반응 방정식

benzyloxyacetaldehyde

ethylene glycol

p-toluenesulfonic acid monohydrate

sodium hydroxide

→

title compound

수율 77.5%

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

수율 77.5%

용매

toluene

ethyl acetate

반응 조건

후처리

1. 1
   workup.STIRRINGfurther stirred at 150° C. for 3 hours
2. 2
   온도After cooled on ice
3. 3
   기타An organic layer was separated
4. 4
   세척washed with water (three times)
5. 5
   건조The organic layer was dried over anhydrous sodium sulfate
6. 6
   농축concentrated
7. 7
   기타The 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
   농축Desired fractions were concentrated

실험 절차

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.

출처