Sodium Hydroxide → 2-(Benzyloxy)-4-iodobenzoic acid

Participants

Reaction Steps

A 2.0 mol/L aqueous solution of sodium hydroxide (4.1 mL) was added to a solution mixture of methyl 2-(benzyloxy)-4-iodobenzoate (1.0 g) in dioxane (5.0 mL) and methanol (5.0 mL), followed by stirring at room temperature for 2 hours. The solvent was evaporated under reduced pressure, and water was added to the residue. After adjusting the pH to 2.5 with 6.0 mol/L hydrochloric acid under ice-cooling, ethyl acetate was added. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. Hexane and diisopropyl ether were added to the obtained residue, and the resulting solid substance was collected by filtration to obtain 0.93 g of 2-(benzyloxy)-4-iodobenzoic acid as a white solid.

Provenance & Evidence