Water → 3-Fluoro-4-nitrobenzoic acid

HRID 1760841Notes

Reaction equation

HRID 1760841 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH3:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].S(=O)(=O)(O)[OH:13].[OH2:17]>>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9])[C:11]([OH:13])=[O:17]

Participants

4

Reactant 3

HCID 962Water2×HCID 1118Sulfuric AcidHCID 67966Benzene, 2-fluoro-4-methyl-1-nitro-

Product 1

HCID 2306533-Fluoro-4-nitrobenzoic acidYield 68%

Procedure

A solution of 3-fluoro-4-nitrotoluene (2 g, 12.82 mmole) in 13 mL water, containing 5.72 g of Na2Cr2O7, was treated dropwise with 14.2 mL of concentrated sulfuric acid, stirred at room temperature for one hour and then diluted with 20 mL of water. The mixture was filtered and the recovered solid was gently heated in 50 mL 2% sodium hydroxide solution. The resulting solution was cooled and filtered and the filtrate was acidified with concentrated HCl. The aqueous phase was extracted with two 100 mL portions of ethyl acetate, the combined extracts were washed with 100 mL of aqueous saturated sodium chloride solution, dried over MgSO4, filtered and concentrated in vacuo to give 1.6 g (68%) of 3-fluoro-4-nitrobenzoic acid as a yellow solid.

Workup

  1. filtrationThe mixture was filtered
  2. temperaturethe recovered solid was gently heated in 50 mL 2% sodium hydroxide solution
  3. temperatureThe resulting solution was cooled
  4. filtrationfiltered
  5. extractionThe aqueous phase was extracted with two 100 mL portions of ethyl acetate
  6. washthe combined extracts were washed with 100 mL of aqueous saturated sodium chloride solution
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c395f20ddb2f4b5f81d6962436d7bf8d
Source dataset
uspto-grants-2005_01
Patent number
US06844466B2

Reaction notes

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