3-Methyl-2-nitrobenzoic acid → 2-Methyl-3-nitrobenzoic acid
Reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5]=1[C:13](O)=O)([O-:3])=[O:2].CC1C([N+]([O-])=O)=C(C=CC=1)C(O)=O>>[CH3:13][C:5]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([OH:9])=[O:8]Participants
Procedure
The disadvantage of this synthesis route is the poor availability of the starting substance 2-methyl-3-nitrobenzoic acid. In Kulic et al., J. Gen. Chem. USSR (Engl.), 60, 2118 (1990), the oxidation of 2,3-dimethylnitrobenzene to 2-methyl-3-nitrobenzoic acid is carried out using aqueous potassium permanganate in the presence of a phase-transfer catalyst at 75° C. In this process, 2-methyl-3-nitrobenzoic acid is not obtained as a pure product, but as a mixture with 3-nitrophthalic acid and smaller amounts of 3-methyl-2-nitrobenzoic acid. A complicated purification is necessary in order to obtain pure 2-methyl-3-nitrobenzoic acid from the crude product. This is at the expense of the yield. A further serious disadvantage is the extremely poor space yield of the oxidation reaction. Per 100 ml of water, only 2.4 g of 2,3-dimethylnitrobenzene are employed (see p. 2121). Moreover, manganese dioxide, which has to be disposed of, is formed during the permanganate oxidation.
Workup
- customA complicated purification
Sources & evidence
- ORD record
- ord-af48d944f0fd41a1bbd2cf8da4479d37
- Source dataset
- uspto-grants-1999_06
- Patent number
- US05910605
Reaction notes
Loading…