Nitric Acid → 5-Fluoro-2-nitrobenzoic acid

HRID 1292599Notes

Reaction equation

HRID 1292599 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.[N+:16]([O-])([OH:18])=[O:17]>O>[F:1][C:2]1[CH:10]=[CH:9][C:8]([N+:16]([O-:18])=[O:17])=[C:4]([CH:3]=1)[C:5]([OH:7])=[O:6]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric Acid2×HCID 99683-Fluorobenzoic Acid

Product 1

HCID 27374205-Fluoro-2-nitrobenzoic acidYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

841 g of 3-fluorobenzoic acid were placed in 3261 g of 100% strength by weight sulphuric acid and the mixture was cooled to +10° C. 1147 g of nitrating acid comprising 67% by weight of 100% strength by weight sulphuric acid and 33% by weight of 100% strength by weight nitric acid were then added. After the reaction was completed, the mixture contained approximately 1.65% by weight of wrong isomers. The mixture was added to 10 1 of water and then cooled to room temperature. The solid product precipitated out was filtered off and then washed 3 times, each time with 2 1 of water, and dried. 957.8 g of 5-fluoro-2-nitro-benzoic acid (calculated as 100% pure product) were obtained, which corresponds to 86.3% of theory. The product contained 0.17% by weight of 3-fluoro-2-nitro-benzoic acid.

Workup

  1. temperaturethe mixture was cooled to +10° C
  2. additionwere then added
  3. customThe solid product precipitated out
  4. filtrationwas filtered off
  5. washwashed 3 times
  6. dry with materialeach time with 2 1 of water, and dried

Sources & evidence

ORD record
ord-91ac9f497816418a80043333c57f330c
Source dataset
uspto-grants-1998_05
Patent number
US05756831

Reaction notes

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