[OH-].[Na+].[OH:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1.Br[CH:14]([OH:17])[CH2:15][CH3:16]>CCO>[OH:17][CH2:14][CH2:15][CH2:16][O:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1An aqueous solution of NaOH (1 mol) and KI (0.05 mmol) was added to a solution of 4-hydroxybenzoic acid (0.5 mmol) and 400 mL EtOH solution under a nitrogen atmosphere and stirred. After stirring for 30 minutes, an EtOH solution including bromopropanol (0.55 mmol) was dropped thereinto, and then, reacted for 24 hours after elevating to 80° C. A solvent was removed from a reaction product and hydrochloric acid-treatment was carried out. A solid phase was isolated through filteration, and 4-(3-hydroxypropoxy)benzoic acid as a compound of Formula 4 was synthesized.
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