Hydrochloric Acid → 3-Ethoxy-4-nitrobenzoic acid

HRID 2234442Notes

Reaction equation

HRID 2234442 reaction equation
F[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([OH:7])=[O:6].[OH-].[K+].Cl.[CH2:17]([OH:19])[CH3:18]>O>[CH2:17]([O:19][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([OH:7])=[O:6])[CH3:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14797Potassium HydroxideHCID 2306533-Fluoro-4-nitrobenzoic acid

Product 1

HCID 223975093-Ethoxy-4-nitrobenzoic acidYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-fluoro-4-nitrobenzoic acid (Apollo Scientific; 15 g, 81 mmol) and potassium hydroxide (10.5 g, 186.3 mmol) were stirred together in ethanol (150 mL) at ambient temperature. The reaction mixture was slowly heating to reflux over 10 minutes. The reaction refluxed vigorously and a solid precipitate formed. The reaction was cooled, diluted with water (100 mL) and acidified with 2N HCl to give a precipitate which was filtered, washed with water and air dried to yield the title compound as a pale brown solid (16.88 g, 99%)

Workup

  1. temperatureThe reaction mixture was slowly heating
  2. temperatureto reflux over 10 minutes
  3. temperatureThe reaction refluxed vigorously
  4. customa solid precipitate formed
  5. temperatureThe reaction was cooled
  6. customto give a precipitate which
  7. filtrationwas filtered
  8. washwashed with water and air
  9. customdried

Sources & evidence

ORD record
ord-ddd8919072ce45398457f4de8a3a2927
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

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