Ethyl Acetate → 3-Hydroxy-2-nitrobenzoic acid

HRID 1672459Notes

Reaction equation

HRID 1672459 reaction equation
Cl[C:2]1[C:3]([N+:11]([O-:13])=[O:12])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[OH-].[K+].C(OCC)(=[O:18])C>O>[OH:18][C:2]1[C:3]([N+:11]([O-:13])=[O:12])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 14797Potassium HydroxideHCID 209023-Chloro-2-nitrobenzoic acid

Product 1

HCID 2932913-Hydroxy-2-nitrobenzoic acidYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-chloro-2-nitrobenzoic acid (30 g, 0.15 mol) and KOH (120 g, 2.14 mol) were dissolved in water (150 mL). The mixture was heated at reflux for 12 h. TLC (petroleum ether:ethyl acetate=1:1) showed the reaction was complete. The pH of mixture was adjusted to 3. The resulting mixture was extracted with ethyl acetate (2×300 mL). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated in vacuo to give the title compound (40 g, 100%) as a brown solid. 1H NMR (400 MHz, DMSO): δ 11.193 (s, 1H), 7.476 (t, 1H), 7.367 (d, 1H), 7.268 (d, 1H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 12 h
  3. extractionThe resulting mixture was extracted with ethyl acetate (2×300 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-daef83239beb4bc58b40c580070471f7
Source dataset
uspto-grants-2011_08
Patent number
US07998978B2

Reaction notes

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