(2,3,4-Trimethoxy-6-methylphenyl)(2,5-dichloro-3-trifluoromethyl-4-pyridyl)methanol → 2,3,4-Trimethoxy-6-methylbenzoyl-2,5-dichloro-3-trifluoromethylpyridine
Reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=[C:5]([CH3:13])[C:4]=1[CH:14]([C:16]1[C:21]([Cl:22])=[CH:20][N:19]=[C:18]([Cl:23])[C:17]=1[C:24]([F:27])([F:26])[F:25])[OH:15]>C1(C)C=CC=CC=1.[O-2].[O-2].[Mn+4]>[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=[C:5]([CH3:13])[C:4]=1[C:14]([C:16]1[C:21]([Cl:22])=[CH:20][N:19]=[C:18]([Cl:23])[C:17]=1[C:24]([F:27])([F:26])[F:25])=[O:15]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
14 g of manganese dioxide was added to a solution having 3.5 g (8.2 mmol) of (2,3,4-trimethoxy-6-methylphenyl)(2,5-dichloro-3-trifluoromethyl-4-pyridyl)methanol obtained in Step (b) dissolved in 100 ml of toluene, followed by stirring under reflux with heating for 6 hours. The mixture was cooled and then subjected to filtration, and toluene was distilled off under reduced pressure. The crude product was purified by silica gel column chromatography to obtain 3.1 g (yield: 89%) of 4-(2,3,4-trimethoxy-6-methylbenzoyl)-2,5-dichloro-3-trifluoromethylpyridine (melting point 106 to 109° C.).
Workup
- temperatureunder reflux
- temperaturewith heating for 6 hours
- temperatureThe mixture was cooled
- filtrationsubjected to filtration, and toluene
- distillationwas distilled off under reduced pressure
- customThe crude product was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-f67e55298d3e4191910e6cac59e38a51
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08653113B2
Reaction notes
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