Water → HCID 19009247, compound

HRID 1742482Notes

Reaction equation

HRID 1742482 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[C:7]([CH3:10])[C:6]([O:11][CH3:12])=[C:5]([CH3:13])[C:4]=1[OH:14].[H-].[Na+].F[C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1.O>CN(C)C=O>[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[C:7]([CH3:10])[C:6]([O:11][CH3:12])=[C:5]([CH3:13])[C:4]=1[O:14][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 9590p-FluoronitrobenzeneHCID 24758Sodium hydrideHCID 190092542,5-Dimethoxy-3,4,6-trimethylphenol

Product 1

HCID 19009247HCID 19009247, compoundYield 41.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

5.8 g of 2,5-dimethoxy-3,4,6-trimethylphenol [prepared as described in step (a) above] in 10 ml of dimethylformamide were added to a suspension of 1.4 g of sodium hydride (as a 55% w/w dispersion in mineral oil) in 50 ml of dimethylformamide, whilst ice-cooling, and the mixture was stirred at room temperature for 2 hours. At the end of this time, a solution of 4.6 g of p-fluoronitrobenzene in 10 ml of dimethylformamide was added to the mixture, whilst ice-cooling. The mixture was then stirred at room temperature for 1 hour, and then at 80° C. for 7 hours. At the end of this time, the mixture was poured into water, and the resulting crude oil was extracted with benzene. The benzene extract was washed with water and dried over anhydrous sodium sulfate. The solvent was then removed by distillation under reduced pressure, and the resulting oil was purified by column chromatography through silica gel, using a 4:1 by volume mixture of benzene and hexane, followed by benzene alone, as the eluent, to give 3.9 g of the title compound.

Workup

  1. temperaturewhilst ice-cooling
  2. temperaturecooling
  3. stirringThe mixture was then stirred at room temperature for 1 hour
  4. waitat 80° C. for 7 hours
  5. extractionthe resulting crude oil was extracted with benzene
  6. extractionThe benzene extract
  7. washwas washed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. customThe solvent was then removed by distillation under reduced pressure
  10. customthe resulting oil was purified by column chromatography through silica gel
  11. additionby volume mixture of benzene and hexane

Sources & evidence

ORD record
ord-bda9f57ac84c46869eaa4f10e64b6162
Source dataset
uspto-grants-1994_08
Patent number
US05338855

Reaction notes

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