Water → 5-Formyl-2-hydroxy-3-methyl-benzoic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of HMTA (1,3,5,7-Tetraaza-tricyclo[3.3.1.13,7]decane, 8.43 g, 60.2 mmol) in TFA (100 mL) is added 2-hydroxy-3-methyl-benzoic acid methyl ester (5 g, 30.1 mmol) and the reaction is refluxed (78° C.) overnight. The reaction is cooled to 50° C. and water (400 mL) is added with stirring. The mixture is stirred at 50° C. for 2 h then cooled to RT and extracted with EtOAc (2×200 mL). The combined organic layers are washed with brine (75 mL), dried over anhydrous MgSO4 and concentrated in vacuo. The residue is purified by flash column chromatography (120 silica gel, gradient elution: 0-50% EtOAc in heptane) to give product (281) as off-white solid (5.05 g, 86%).

Provenance & Evidence