C([O:4][C:5]1[CH:6]=[CH:7][C:8]([N:16]2[C:20]([CH3:21])=[N:19][N:18]=[N:17]2)=[C:9]([CH:15]=1)[C:10]([O:12][CH2:13][CH3:14])=[O:11])(=O)C.[O-]CC.[K+].O.[Cl-].[NH4+]>CN(C=O)C>[OH:4][C:5]1[CH:6]=[CH:7][C:8]([N:16]2[C:20]([CH3:21])=[N:19][N:18]=[N:17]2)=[C:9]([CH:15]=1)[C:10]([O:12][CH2:13][CH3:14])=[O:11]Ethyl 5-acetoxy-2-(5-methyltetrazol-1-yl)benzoate (164 g, 0.565 mol) was dissolved in 500 mL of DMF and immersed in a water bath. Potassium ethoxide (52.3 g, 0.621 mol) was added to this solution portionwise, keeping the reaction temperature below 40° C. After 30 minutes, the reaction was poured into 4 L of water and ammonium chloride was added to the solution until the product precipitated. After one hour of stirring, the precipitate was filtered and dried under a flow of air to give 98.5 g of ethyl 5-hydroxy-2-(5-methyltetrazol-1-yl)benzoate as a white solid.
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