Lithium Hydroxide → m-Hydroxyhippuric acid

Reaction equation

[Li+].[OH-].C([O:5][C:6](=[O:18])[CH2:7][NH:8][C:9](=[O:17])[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([OH:16])[CH:11]=1)C>C1COCC1.CO>[OH:16][C:12]1[CH:11]=[C:10]([CH:15]=[CH:14][CH:13]=1)[C:9]([NH:8][CH2:7][C:6]([OH:18])=[O:5])=[O:17]

Participants

Procedure

LiOH (75 mg in 2 mL water) was added to (3-hydroxy-benzoyl amino)-acetic acid ethyl ester (100 mg, 0.45 mmol) in a mixture of THF and MeOH mixture. This was followed by the addition of to the reaction mixture. The resulting mixture was stirred at room temperature overnight. The THF and MeOH were then evaporated under reduced pressure and the resulting residue was acidified to pH 2 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 (3-hydroxy-benzoyl amino)-acetic acid in 89% yield. 1H NMR (DMSO-D6): δ 12.4 (s, 1H), 9.6 (s, 1H), 8.7 (t, 1H), 7.2 (d, 3H), 6.9 (m, 1H), 4.0 (d, 2H).