Potassium Hydroxide → 2-(4-Chloro-3-nitrophenyl)-2-methylpropanoic acid
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:14])([CH3:13])[C:9]([O:11]C)=[O:10])=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16].[OH-].[K+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:14])([CH3:13])[C:9]([OH:11])=[O:10])=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
In 200 ml of methanol was dissolved 75.5 g of methyl 2-(4-chloro-3-nitrophenyl)-2-methylpropionate. Under ice cooling, 70 ml of an aqueous solution of 49.3 g of potassium hydroxide was added dropwise and the mixture was stirred at room temperature for 3 hours. The reaction mixture was concentrated under reduced pressure. To the residue were added water and n-hexane to separate the mixture into layers. Concentrated hydrochloric acid was added to the aqueous layer to adjust its pH to 2 or less, followed by extraction with ethyl acetate. The ethyl acetate layer was washed successively with water and brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was recrystallized from ethyl acetate to obtain 53.1 g of the title compound.