Tetraethylene Glycol → HCID 14691830, compound

HRID 1067180Notes

Reaction equation

HRID 1067180 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[CH2:11]([OH:23])[CH2:12][O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][OH:22].[OH-].[K+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[OH:22][CH2:21][CH2:20][O:19][CH2:18][CH2:17][O:16][CH2:15][CH2:14][O:13][CH2:12][CH2:11][O:23][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8200Tetraethylene GlycolHCID 9590p-FluoronitrobenzeneHCID 14797Potassium Hydroxide

Product 1

HCID 14691830HCID 14691830, compound

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 1140TolueneSolvent

Procedure

18.16 g (128.7 mmol) of 4-fluoronitrobenzene is added to 100 g (515.0 mmol) of tetraethylene glycol, 73 g (1300 mmol) of finely powdered potassium hydroxide and 500 mg of tetrabutylammonium hydrogen sulfate in 500 ml of toluene at 0° C., and it is stirred overnight at room temperature. 1000 ml of saturated common salt solution is; added, the organic phase is separated and it is dried on magnesium sulfate. It is evaporated to dryness in a vacuum, and the residue is chromatographed in silica gel (mobile solvent: methylene chloride/isopropanol=15:1).

Workup

  1. additionadded
  2. customthe organic phase is separated
  3. customit is dried on magnesium sulfate
  4. customIt is evaporated to dryness in a vacuum
  5. customthe residue is chromatographed in silica gel (mobile solvent: methylene chloride/isopropanol=15:1)

Sources & evidence

ORD record
ord-e263065a473c4c2eafee68c35b42b657
Source dataset
uspto-grants-2001_06
Patent number
US06248306B1

Reaction notes

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