Lithium Hydroxide → Salicyluric Acid

Participants

Reaction Steps

LiOH in water (82 mg in 2 mL of water) was added dropwise to (2-hydroxy-benzoyl amino)-acetic acid ethyl ester (110 mg, 0.49 mmol) in a mixture of THF and MeOH. The THF and MeOH were evaporated under reduced pressure and the residue was acidified using 10% citric acid solution. The product was extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure to afford (2-hydroxybenzoyl amino)-acetic acid in 93% yield. 1H NMR (DMSO-D6): δ 12.8 (s, 1H), 12.2 (s, 1H), 9.2 (t, 1H), 7.9 (d, 1H), 7.5 (dt, 1H), 7.0 (d, 2H), 4.0 (d, 2H).

Provenance & Evidence