Nitric Acid → 2,4,5-Trifluoro-3-methyl-6-nitrobenzoic acid
Reaction equation
[F:1][C:2]1[C:10]([CH3:11])=[C:9]([F:12])[C:8]([F:13])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.[N+:19]([O-])([OH:21])=[O:20]>>[F:1][C:2]1[C:10]([CH3:11])=[C:9]([F:12])[C:8]([F:13])=[C:7]([N+:19]([O-:21])=[O:20])[C:3]=1[C:4]([OH:6])=[O:5]Participants
Procedure
A 43.4 g (0.21 mol) portion of 2,4,5-trifluoro-3-methylbenzoic acid was added to 120 ml of concentrated sulfuric acid under ice cooling. Thereto was added dropwise fuming nitric acid (d 1.52) in such a manner that the reaction temperature did not exceed 30° C. After completion of the dropwise addition, this was stirred for 1 hour at room temperature. After completion of the reaction, the reaction solution was poured into 1.5 liters of ice water to collect the formed crystals by filtration. The thus obtained crystals were washed with water (100 ml×3) and dissolved in 500 ml of ethyl acetate, and the solution was dried over anhydrous sodium sulfate. The filtrate obtained above was extracted with chloroform (300 ml×4) and dried over anhydrous sodium sulfate. Thereafter, the organic layers were combined and concentrated to yield 50.3 g (quantitative) of the title compound.
Workup
- customdid not exceed 30° C
- additionAfter completion of the dropwise addition
- customAfter completion of the reaction
- customto collect the formed crystals
- filtrationby filtration
- washThe thus obtained crystals were washed with water (100 ml×3)
- dissolutiondissolved in 500 ml of ethyl acetate
- dry with materialthe solution was dried over anhydrous sodium sulfate
- customThe filtrate obtained
- extractionabove was extracted with chloroform (300 ml×4)
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-3545e7628d70459ba425d04715e2eec1
- Source dataset
- uspto-grants-1998_12
- Patent number
- US05849757
Reaction notes
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