Water → (2-Methoxy-6-methylphenyl)methanol

Participants

Reaction Steps

To a solution of 1.0 M lithium aluminium hydride in anhydrous THF (3.6 ml, 3.6 mmol), under nitrogen, was added anhydrous THF (12 ml). Ethyl 2-methyl-6-(methyloxy)benzoate (1 g, 5.2 mmol, ABCR) in anhydrous THF (2 ml) was then added over 5 min with stirring. The solution was stirred for 15 min and then heated at gentle reflux for 100 min. The solution was allowed to cool. A 5% solution of water in ethanol was added dropwise. The solvent was removed in vacuo and acidified using 1 to 2M aqueous HCl. The mixture was extracted with chloroform and the organic solvent removed in vacuo to give the title compound as yellow solid (0.775 g); LCMS: (System 4) MH+=152, tRET=1.78 min.

Provenance & Evidence