Lithium Hydroxide → Benzoic Acid

Participants

Reaction Steps

A stirred solution of 4-[(3-acetoxybenzylamino)sulfonyl]-2-chlorobenzoic acid methyl ester (163 mg; 0.41 mmol) in methanol (3 mL) and tetrahydrofuran (3 mL) was treated at room temperature with an aqueous 1 N lithium hydroxide solution (1.65 mL). After 2 hr the volatiles were removed under reduced pressure and the residual material was dissolved in water (15 mL) and the solution filtered through Celite. The filtrate was acidified with 1 N HCl (2 mL) and extracted with ethyl acetate (3×10 mL). After the extracts were backwashed in turn with brine, they were combined, dried (Na2SO4) and evaporated in vacuo to furnish 140 mg of 2-chloro-4-[(3)-hydroxybenzylamino)sulfonyl]benzoic acid. A small sample of the product was crystallized from ethyl acetate-hexane to give a colorless solid, mp 167-169° C. FAB LRMS: (C14H12ClNO5S) Obs. Mass 342 Calcd. Mass 342 (M+H).

Provenance & Evidence