Reaktion #1169050

Reaktionsgleichung

5-methoxysalicylaldehyde

LiAlH4

HCl

LiAlH4

→

title compound

Ausbeute 77.0%

2-hydroxymethyl-4-methoxyphenol

Ausbeute 77.0%

Lösungsmittel

ether

ether

ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGwith subsequent stirring at room temperature for 30 minutes
2. 2
   workup.ADDITIONTo the reaction solution was added ice carefully
3. 3
   FiltrationAfter filtering off insoluble materials
4. 4
   Sonstigethe ether layer was separated from the filtrate
5. 5
   Extraktionthe aqueous phase was further extracted with ether
6. 6
   WaschenThe combined ether layers were washed with saturated sodium chloride solution
7. 7
   Trocknendried over anhydrous sodium sulfate
8. 8
   SonstigeThe solvent was removed under reduced pressure
9. 9
   Waschenthe residue was washed with ether-hexane
10. 10
    Filtrationfiltered

Vorschrift

Under ice cooling, the solution of 5-methoxysalicylaldehyde (5 g) in ether (20 ml) was slowly added dropwise to the suspension of LiAlH4 (0.75 g) in ether (50 ml). After stirring at room temperature for 2 hours, another addition of LiAlH4 (0.5 g) was carried out under ice cooling, with subsequent stirring at room temperature for 30 minutes. To the reaction solution was added ice carefully, followed by sequential addition of 1N HCl and ether. After filtering off insoluble materials using Celite™, the ether layer was separated from the filtrate, and then, the aqueous phase was further extracted with ether. The combined ether layers were washed with saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was washed with ether-hexane and filtered to give the title compound (3.9 g; 77%).

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