Potassium Hydroxide → 2-(2,4-dichlorophenoxy)-2-methylpropanoic acid
Reaction equation
[OH-].[K+].[Cl:3][C:4]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:5]=1[O:6][C:7]([CH3:14])([CH3:13])[C:8]([O:10]CC)=[O:9]>O.CCO>[Cl:3][C:4]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:5]=1[O:6][C:7]([CH3:14])([CH3:13])[C:8]([OH:10])=[O:9]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of KOH (2.48 g, 44.2 mmol, 15 eq) in H2O (12 mL) was added a solution of ethyl 2-(2,4-dichlorophenoxy)-2-methylpropionate (compound 5; 0.80 g, 2.89 mmol) in EtOH (12 mL). The solution was stirred at room temperature for 4 hours, then excess EtOH was removed under vacuum. The remaining aqueous solution was washed with EtOAc (10 mL), then acidified with concentrated aqueous HCl. The aqueous mixture was then extracted with EtOAc (10 mL), and the organic extract dried over Na2SO4, filtered, and evaporated to yield a thick, colorless oil which was used without further purification: 1H NMR (CDCl3) δ 7.42-7.41 (d, 1H), 7.19-7.15 (dd, 1H), 7.04-7.01 (d, 1H), 1.64 (s, 6H).