Potassium Hydroxide → 2-(Benzylsulfanyl)benzoic acid
Reaction equation
C([O:8][C:9](=[O:24])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[S:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)C1C=CC=CC=1.[OH-].[Na+].[OH-].[K+]>>[CH2:17]([S:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[C:9]([OH:24])=[O:8])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1Participants
4
Procedure
To a suspension of 2-benzylsulfanyl benzoic acid benzyl ester 2 (113 mg, 0.34 mmol) was added 1.6 mL of 1N NaOH. KOH (1 pellet) was added and the reaction was continued overnight. The acetone was removed and a small amount of water was added. The aqueous solution was washed with CH2Cl2(3). The aqueous phase was acidified until pH of 2–3 was reached then extracted with CH2Cl2(3X), dried with MgSO4 and filtered and concentrated to give a white solid.