Reaktion #1732689

Reaktionsgleichung

benzyloxyacetaldehyde

1,1-bis(hydroxymethyl)cyclopropane

→

title compound

Ausbeute 78.2%

6-((benzyloxy)methyl)-5,7-dioxaspiro[2.5]octane

Ausbeute 78.2%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas refluxed for 2 hours
2. 2
   Sonstigewhile removing water by the Dean-Stark apparatus
3. 3
   workup.ADDITIONtriethylamine (4 ml) was added to the reaction mixture
4. 4
   workup.DISTILLATIONthe solvent was distilled off
5. 5
   SonstigeThe residue was purified by silica gel column chromatography (silica gel: 200 g, elution solvent: ethyl acetate/heptane=5/95 to 1/9)

Vorschrift

A mixture of benzyloxyacetaldehyde (5 g, 33.3 mmol), 1,1-bis(hydroxymethyl)cyclopropane (4.08 g, 40 mmol), p-toluenesulfonic acid monohydrate (287 mg, 1.51 mmol) and toluene (70 ml) was refluxed for 2 hours while removing water by the Dean-Stark apparatus. After the reaction mixture was cooled to room temperature, triethylamine (4 ml) was added to the reaction mixture and the solvent was distilled off. The residue was purified by silica gel column chromatography (silica gel: 200 g, elution solvent: ethyl acetate/heptane=5/95 to 1/9) to obtain the title compound (6.1 g, yield: 78.2%) as a light yellow oil.

Quelle