Methane → HCID 18314473, compound

HRID 636044Notes

Reaction equation

HRID 636044 reaction equation
O.C(O)(=O)C.[Cl:6][C:7]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][C:8]=1[CH:9]([OH:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[O:16][CH3:17].CO.O.C>O.[O-2].[Cr+6].[O-2].[O-2]>[Cl:6][C:7]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][C:8]=1[C:9]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[O:16][CH3:17])=[O:18]

Participants

7

Reactant 4

HCID 297MethaneHCID 18314511HCID 18314511, compoundHCID 21899381Acetic acid--water (1/1)HCID 22242641Methanol--water (1/1)

Product 1

HCID 18314473HCID 18314473, compound

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 962WaterSolvent2×

Procedure

A solution of chromium(VI) oxide (91.0 g, 0.919 mol) in a water/acetic acid solution (1:4) is added portionwise to 2-chloro-2′-methoxy-5-nitrobenzhydrol (64.2 g, 0.219 mol) while maintaining the reaction mixture temperature at 25° C. to 35° C. The reaction mixture is then stirred at 25° C. to 35° C. for one hour, cooled, diluted with water, and concentrated in vacuo to obtain a residue. The residue is diluted with water, and extracted with methylene chloride. The organic extracts are combined, dried over anhydrous sodium sulfate, mixed with silica gel (10 g), and filtered. The filtrate is concentrated in vacuo to obtain an oil. A solution of the oil in a methanol/water solution is decolorized with charcoal and concentrated in vacuo to yield a residue. Column chromatography of the residue using silica gel and methylene chloride/hexanes solutions gives the title product as a white solid.

Workup

  1. temperaturewhile maintaining the reaction mixture temperature at 25° C. to 35° C
  2. temperaturecooled
  3. concentrationconcentrated in vacuo
  4. customto obtain a residue
  5. extractionextracted with methylene chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. additionmixed with silica gel (10 g)
  8. filtrationfiltered
  9. concentrationThe filtrate is concentrated in vacuo
  10. customto obtain an oil
  11. concentrationconcentrated in vacuo
  12. customto yield a residue

Sources & evidence

ORD record
ord-716e92e7d46c40d4bc911ac8f289d437
Source dataset
uspto-grants-2001_02
Patent number
US06191275B1

Reaction notes

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