Hydrochloric Acid → Ethyl 2-hydroxy-3-nitrobenzoate

HRID 912423Notes

Reaction equation

HRID 912423 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

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 68073-Nitrosalicylic acid

Product 1

HCID 12157235Ethyl 2-hydroxy-3-nitrobenzoateYield 86%

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%).

Workup

  1. concentrationconcentrated in a vacuum
  2. additiondiluted with ethyl acetate
  3. washThis dilution was washed with an aqueous saturated sodium bicarbonate solution
  4. dry with materialan aqueous saturated NaCl solution, dried over magnesium sulfate
  5. concentrationconcentrated in a vacuum
  6. customThe concentrate was purified

Sources & evidence

ORD record
ord-a2383fa2da67456ab7326ffbfd54569c
Source dataset
uspto-grants-2011_09
Patent number
US08026235B1

Reaction notes

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