Sodium Hydroxide → 2-Benzyl-4-nitro-benzoic acid
Reaction equation
[OH-].[Na+].C[C:4]1[C:5]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:6]([CH:10]=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])[C:7]([OH:9])=[O:8]>CO>[CH2:16]([C:5]1[CH:4]=[C:12]([N+:13]([O-:15])=[O:14])[CH:11]=[CH:10][C:6]=1[C:7]([OH:9])=[O:8])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
2N Aqueous sodium hydroxide solution (2.0 mL, 4 mmol) was added to a solution of compound (28) (2.06 mmol) in methanol (10 mL) at ambient temperature. After 2 hrs the reaction mixture was evaporated to remove the methanol and then partitioned between ethyl ether (20 mL) and 2N aqueous sodium hydroxide solution (20 mL). The aqueous phase was acidified to pH⅔ with 2N HCl and extracted with ethyl acetate(3×20 mL). The combined organics were washed with water (20 mL) and brine (20 mL), filtered through phase separating paper and evaporated to yield 2-benzyl-4nitrobenzoic acid (compound 29).