Hydrochloric Acid → 72985-24-1

Participants

Reaction Steps

To a stirring solution of 800 mg of 5-(hydroxymethyl)-2-methylbenzaldehyde in 20 mL of MeOH was added 3.4 g (5.5 mmol) of Oxone. The mixture was stirred at r.t. for 3.75 h and 2 mL of MeOH was added. After 2.5 h, 15 mL of 1N HCl, 45 mL of H2O, and EtOAc were added, and the layers separated. The aqueous layer was extracted, the combined extracts were washed with brine, dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography (30% EtOAc/hexanes) provided 377 mg of methyl 5-(hydroxymethyl)-2-methylbenzoate as a yellow oil with some impurity.

Provenance & Evidence