Sodium Bicarbonate → Methyl 2-hydroxy-6-methoxymethylbenzoate

Participants

Reaction Steps

A solution of methyl 2-bromomethyl-6-(tert-butyldimethylsilyloxy)benzoate (Intermediate 12, 4.26 g) in methanol (63 mL) was stirred and heated at reflux overnight. After cooling, the mixture was basified by addition of solid sodium bicarbonate and then evaporated to dryness. The residue was triturated with DCM and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-25% to give methyl 2-hydroxy-6-methoxymethylbenzoate (1.46 g) as a white crystalline solid.

Provenance & Evidence