(2,3,4-Trimethoxy-6-methylphenyl)(3-chloro-5-trifluoromethyl-4-pyridyl)methanol → 4-(2,3,4-Trimethoxy-6-methylbenzoyl)-3-chloro-5-trifluoromethylpyridine

HRID 243783Notes

Reaction equation

HRID 243783 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]([C:22]([F:25])([F:24])[F:23])=[CH:20][N:19]=[CH:18][C:17]=1[Cl:26])[OH:15]>[O-2].[O-2].[Mn+4].C1(C)C=CC=CC=1>[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]([C:22]([F:25])([F:23])[F:24])=[CH:20][N:19]=[CH:18][C:17]=1[Cl:26])=[O:15]

Participants

4

Reactant 1

HCID 12151302(2,3,4-Trimethoxy-6-methylphenyl)(3-chloro-5-trifluoromethyl-4-pyridyl)methanol

Product 1

HCID 121513034-(2,3,4-Trimethoxy-6-methylbenzoyl)-3-chloro-5-trifluoromethylpyridineYield 94.2%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Procedure

45 g of manganese dioxide was added to a toluene 220 ml solution of 15.9 g (40.6 mmol) of (2,3,4-trimethoxy-6-methylphenyl)(3-chloro-5-trifluoromethyl-4-pyridyl)methanol obtained in Step (b), followed by stirring under reflux with heating for 2 hours. The mixture was subjected to filtration, and the solvent was distilled off under reduced pressure to obtain 14.9 g (yield: 94%) of 4-(2,3,4-trimethoxy-6-methylbenzoyl)-3-chloro-5-trifluoromethylpyridine.

Workup

  1. temperatureunder reflux
  2. temperaturewith heating for 2 hours
  3. filtrationThe mixture was subjected to filtration
  4. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-7d61702f857843c1b3f0a76636ffc2ca
Source dataset
uspto-grants-2014_02
Patent number
US08653277B2

Reaction notes

Loading…