Lithium Hydroxide → 3-Methyl-4-(1-piperidinyl)benzoic acid

Participants

Reaction Conditions

Reaction Steps

Lithium hydroxide (2.5 g; 103 mmol; 5 eq.) was added to a solution of methyl 3-methyl-4-piperidin-1-ylbenzoate (4.8 g; 20.6 mmol; 1 eq.) in THF (100 mL) and water (5 mL) and the reaction mixture was stirred at 50° C. for 12 hours. The solvent was removed in vacuo, the residue diluted with water and the aqueous layer washed with DCM (2×50 mL). The aqueous layer was acidified to pH 4 with conc. HCl and extracted with ethyl acetate (2×100 mL). The combined organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo to afford the title compound (4.0 g, 89%) as a yellow solid.

Provenance & Evidence