Lithium Hydroxide → HCID 23436260, compound

Participants

Reaction Steps

The 4-(3-pyridyloxymethyl)-2-(2-methylphenyl)benzoic acid methyl ester prepared in Example 204D (160 mg, 0.48 mmol) was dissolved in 5 mL of methanol and 1 mL of saturated aqueous LiOH was added. The reaction was heated to reflux for 1 hour. The reaction was then evaporated and 1 mL of formic acid was added to acidify the crude product 1 to pH=3. The reaction was evaporated again to remove formic acid and 5 mL of ethyl acetate and 1 mL of H2O were added to completely solubilize the reaction mixture. The aqueous layer was extracted with ethyl acetate (3×5 mL) and all the ethyl acetate layers were combined and dried over Na2SO4, filtered and evaporated to give 4-(3-pyridyloxymethyl)-2-(2-methylphenyl)benzoic acid (131 mg, 86%) as an oil.

Provenance & Evidence