Lithium Hydroxide → 2-methoxy-5-(1H-tetrazol-1-ylmethyl)benzoic acid
Reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([CH2:13][N:14]2[CH:18]=[N:17][N:16]=[N:15]2)=[CH:9][C:4]=1[C:5]([O:7]C)=[O:6].[OH-].[Li+]>C(OCC)(=O)C.CCCCCC>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([CH2:13][N:14]2[CH:18]=[N:17][N:16]=[N:15]2)=[CH:9][C:4]=1[C:5]([OH:7])=[O:6]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Combine methyl 2-methoxy-5-(1H-tetrazol-1-ylmethyl)benzoate (0.45 g, 1.73 mmol) and methanol/tetrahydrofuran (1/1, 10 mL). Add a 1 M aqueous solution of lithium hydroxide (5.8 mL, 5.8 mmol). After 4 hours, partition the reaction mixture between water and ethyl acetate. Acidify the aqueous with a 10% aqueous citric acid solution, extract four times with ethyl acetate, combine the ethyl acetate layers, dry the organic layer over Na2SO4, filter, and evaporate in vacuo to give 2-methoxy-5-(1H-tetrazol-1-ylmethyl)benzoic acid: Rf=0.60 (silica gel, 1/1 methanol/dichloromethane).