Lithium Hydroxide → 4-[(3,4-Dichlorophenyl)methoxy]benzoic acid

Participants

Reaction Steps

To a solution of methyl 4-[(3,4-dichlorobenzyl)oxy]benzoate (Preparation 8, 750 mg; 2.41 mmol) in tetrahydrofuran (12 mL) was added an aqueous solution of lithium hydroxide (2 M, 6 mL, 12 mmol) and the reaction stirred at reflux for 4 hours. Upon consumption of starting material the reaction mixture cooled to room temperature and solvent removed in vacuo. The resulting residue was dissolved in water (15 mL) and acidified with 2M hydrochloric acid solution. The aqueous phase was then extracted with dichloromethane (3×25 mL). The combined organic extracts were dried over magnesium sulphate, filtered and evaporated in vacuo to give the title compound (620 mg, 87%) as a white solid.

Provenance & Evidence