Hydrochloric Acid → 2-Ethoxy-4-methoxybenzoic acid

Reaction equation

C([O:3][C:4](=[O:16])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:6]=1[O:13][CH2:14][CH3:15])C.[OH-].[K+].Cl>C(O)C>[CH2:14]([O:13][C:6]1[CH:7]=[C:8]([O:11][CH3:12])[CH:9]=[CH:10][C:5]=1[C:4]([OH:16])=[O:3])[CH3:15]

Participants

Procedure

2-Ethoxy-4-methoxybenzoic acid ethyl ester (13 g, 58 mmol) was suspended in ethanol (150 mL). This was treated with potassium hydroxide (40 mL, ˜4 M) and refluxed for 1 h. The reaction was cooled and poured into cold aqueous hydrochloric acid (300 mL, 2 M) and extracted into dichloromethane (3×200 mL). The organic layers were washed with brine and dried over anhydrous magnesium sulfate. The solids were filtered off, and the filtrate was evaporated to dryness to give 2-ethoxy-4-methoxybenzoic acid (9.5 g, white solid).