Hydrochloric Acid → Ethyl 2-hydroxy-3-nitrobenzoate
Reaction equation
[OH:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Cl.[CH2:15](O)[CH3:16]>>[CH2:15]([O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][CH:9]=[C:10]([N+:11]([O-:13])=[O:12])[C:2]=1[OH:1])[CH3:16]Participants
4
Procedure
To a solution of 2-hydroxy-3-nitrobenzoic acid 10.0 g (55 mmol) in ethanol 100 mL was added dropwise 2 mL of conc. HCl, followed by stirring for 24 hrs under reflex. The mixture was cooled to room temperature, concentrated in a vacuum, and diluted with ethyl acetate. This dilution was washed with an aqueous saturated sodium bicarbonate solution and an aqueous saturated NaCl solution, dried over magnesium sulfate and concentrated in a vacuum. The concentrate was purified using column chromatography (developing solvent: ethylacetate/hexane=1/4) to afford the title compound 10.0 g (yield 86%).