Sodium Hydroxide → 2-Chloro-3-hydroxy-5-nitro-p-anisaldehyde
Reaction equation
C([O:4][C:5]1[C:10]([O:11][CH3:12])=[C:9]([N+:13]([O-:15])=[O:14])[CH:8]=[C:7]([CH:16]=[O:17])[C:6]=1[Cl:18])(=O)C.[OH-].[Na+]>CO>[Cl:18][C:6]1[C:5]([OH:4])=[C:10]([O:11][CH3:12])[C:9]([N+:13]([O-:15])=[O:14])=[CH:8][C:7]=1[CH:16]=[O:17]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
35.8 g of 2-chloro-3-formyl-6-methoxy-5-nitrophenyl acetate are dissolved in 300 ml of methanol. After adding 145 ml of 1N sodium hydroxide solution the mixture is stirred at 23° for 1 hour. After evaporation of the methanol, the residue is diluted with ice-water, made acid with 2N hydrochloric acid and extracted twice with 400 ml of ethyl acetate each time. The organic phases are washed with saturated sodium chloride solution, dried over sodium sulfate and evaporated. The residue is recrystallized from methylene chloride/petroleum ether. There is obtained 2-chloro-3-hydroxy-5-nitro-p-anisaldehyde of m.p. 130°.