Ethanol → Ethyl 2-hydroxy-3-nitrobenzoate

HRID 1809121Notes

Reaction equation

HRID 1809121 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].[CH2:14](O)[CH3:15]>Cl>[CH2:14]([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])[CH3:15]

Participants

4

Reactant 2

HCID 702EthanolHCID 68073-Nitrosalicylic acid

Product 1

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

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

10.0 g (55 mmol) of 2-hydroxy-3-nitrobenzoic acid was dissolved in 100 mL of ethanol 2 mL of concentrated hydrochloric acid was added dropwise thereto and stirred for 24 hr under heat-reflux. The mixture was cooled to room temperature and concentrated under reduced pressure, followed by dilution with ethyl acetate. The diluted solution was washed with saturated sodium bicarbonate solution and saturated sodium chloride solution, then dried over magnesium sulfate and concentrated under reduced pressure. The resulting residue was subjected to column chromatography (ethyl acetate:hexane=1:4) to obtain the title compound (10.0 g, yield: 86%).

Workup

  1. additionwas added dropwise
  2. temperatureunder heat-reflux
  3. concentrationconcentrated under reduced pressure
  4. washThe diluted solution was washed with saturated sodium bicarbonate solution and saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9a5bddc75fdd4659935320fcf0679367
Source dataset
uspto-grants-2013_01
Patent number
US08362012B2

Reaction notes

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