Acetic Acid → 2-Fluoro-4-nitrobenzoic acid
Reaction equation
S(=O)(=O)(O)O.[F:6][C:7]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9]C=1C.[C:17]([OH:20])(=[O:19])[CH3:18]>O.[O-2].[O-2].[O-2].[Cr+6]>[F:6][C:7]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:18]=1[C:17]([OH:20])=[O:19]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 95 °C
Procedure
Concentrated sulfuric acid (32 ml) was added carefully with stirring to a solution of 2-fluoro-4-nitrotoluene (16.5 g, 0.106 mol) in acetic acid (200 ml). The mixture was warmed up to 95° C., and solution of chromium trioxide (37.1 g, 0.371 mol) in water (32 ml) was added dropwise with stirring over 2 h. The mixture was heated with stirring for another 30 minutes, allowed to cool down to r.t., and poured into water (1000 ml). The product was extracted with diethyl ether (3×200 ml). Combined ether layers were washed with water and evaporated to dryness. The residue was dissolved in 10% aqueous potassium carbonate and washed with ether. The aqueous layer was acidified with con. HCl, and the resulting white precipitate filtered and dried (16.3 g, 83%), m.p. 174-177° C.
Workup
- temperatureThe mixture was heated
- stirringwith stirring for another 30 minutes
- temperatureto cool down to r.t.
- extractionThe product was extracted with diethyl ether (3×200 ml)
- washCombined ether layers were washed with water
- customevaporated to dryness
- dissolutionThe residue was dissolved in 10% aqueous potassium carbonate
- washwashed with ether
- filtrationHCl, and the resulting white precipitate filtered
- customdried (16.3 g, 83%), m.p. 174-177° C.
Sources & evidence
- ORD record
- ord-b3df808cf1f1436995c1566a6ebe5db3
- Source dataset
- uspto-grants-2004_06
- Patent number
- US06743811B2
Reaction notes
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