Hydrochloric Acid → 2-Nitro-5-(propan-2-yloxy)benzoic acid

HRID 1070399Notes

Reaction equation

HRID 1070399 reaction equation
[H-].[Na+].[CH:3]([OH:6])([CH3:5])[CH3:4].F[C:8]1[CH:9]=[CH:10][C:11]([N+:17]([O-:19])=[O:18])=[C:12]([CH:16]=1)[C:13]([OH:15])=[O:14].Cl>C1COCC1>[CH:3]([O:6][C:8]1[CH:9]=[CH:10][C:11]([N+:17]([O-:19])=[O:18])=[C:12]([CH:16]=1)[C:13]([OH:15])=[O:14])([CH3:5])[CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 24758Sodium hydrideHCID 27374205-Fluoro-2-nitrobenzoic acid

Product 1

HCID 127191792-Nitro-5-(propan-2-yloxy)benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

60% NaH in oil (950 mg, 23.8 mmol) was added to isopropyl alcohol (4.1 mL) in THF (20 mL) under a nitrogen atmosphere. After stirring for 30 min, 5-fluoro-2-nitrobenzoic acid (2.0 g, 10.8 mmol) was added, and the mixture was heated at reflux for 6 h. Following addition of 2N HCl to adjust the pH to 2, the mixture was extracted, washed with brine, dried (Na2SO4) and concentrated to dryness. Purification by chromatography gave 950 mg of 5-isopropoxy-2-nitro-benzoic acid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 6 h
  3. extractionthe mixture was extracted
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated to dryness
  7. customPurification by chromatography

Sources & evidence

ORD record
ord-921cae88e40f4224a32ba89da7ae2289
Source dataset
uspto-grants-2005_06
Patent number
US06903086B2

Reaction notes

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