Potassium Hydroxide → 4,6-dichloro-3-hydroxy-2-nitrobenzoic acid

HRID 336427Notes

Reaction equation

HRID 336427 reaction equation
[OH-:1].[K+].C(N[C:7]1[C:8]([N+:18]([O-:20])=[O:19])=[C:9]([C:13]([Cl:17])=[CH:14][C:15]=1[Cl:16])[C:10]([OH:12])=[O:11])(=O)C>O>[Cl:16][C:15]1[CH:14]=[C:13]([Cl:17])[C:9]([C:10]([OH:12])=[O:11])=[C:8]([N+:18]([O-:20])=[O:19])[C:7]=1[OH:1]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 10379608HCID 10379608, compound

Product 1

HCID 106584324,6-dichloro-3-hydroxy-2-nitrobenzoic acidYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

A solution of KOH (73.4 g,) in H2O (330 mL) was added to 3-acetamido-4,6-dichloro-2-nitrobenzoic acid 1-5 (38.1 g, 0.130 mol). The resulting brown solution was heated to reflux for 18 h (bath temp 130° C.). The reaction was cooled and extracted with ether. The aqueous layer was then acidified to pH 2 with concentrated HCl and extracted into EtOAc (×4). The combined organic layers were washed with brine (×3), dried over Na2SO4, filtered and concentrated to provide 4,6-dichloro-3-hydroxy-2-nitrobenzoic acid 1-6 as a brown solid (31.0 g, 95%). 1H NMR (400 MHz, d6-DMS) 57.88 (s, 1H).

Workup

  1. temperatureThe resulting brown solution was heated
  2. temperatureThe reaction was cooled
  3. extractionextracted with ether
  4. extractionextracted into EtOAc (×4)
  5. washThe combined organic layers were washed with brine (×3)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-aa4de399079842b5b21dafde531bef90
Source dataset
uspto-grants-2014_11
Patent number
US08889695B2

Reaction notes

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