Hydrochloric Acid → 2-(hydroxymethyl)-4-methoxyphenol

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%).

1. stirringwith subsequent stirring at room temperature for 30 minutes
2. additionTo the reaction solution was added ice carefully
3. filtrationAfter filtering off insoluble materials
4. customthe ether layer was separated from the filtrate
5. extractionthe aqueous phase was further extracted with ether
6. washThe combined ether layers were washed with saturated sodium chloride solution
7. dry with materialdried over anhydrous sodium sulfate
8. customThe solvent was removed under reduced pressure
9. washthe residue was washed with ether-hexane
10. filtrationfiltered

ORD record

ord-3fd9f54b074d4167a284ff76df634988

Source dataset

uspto-grants-1996_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05587392