Glycerol → HCID 19913413, compound

HRID 1090595Notes

Reaction equation

HRID 1090595 reaction equation
[H-].[Na+].[OH:3][CH2:4][CH:5]([CH2:7][OH:8])[OH:6].Cl[C:10]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][C:13]([N+:19]([O-:21])=[O:20])=[CH:12][N:11]=1.[Cl-].[NH4+]>CCCCCC.C1(C)C=CC=CC=1.C(OCC)(=O)C>[OH:6][CH:5]([CH2:7][O:8][C:10]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][C:13]([N+:19]([O-:21])=[O:20])=[CH:12][N:11]=1)[CH2:4][OH:3]

Participants

8

Reactant 4

HCID 753GlycerolHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 757382-Chloro-3,5-dinitropyridine

Product 1

HCID 19913413HCID 19913413, compoundYield 99.3%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

3.3 g of sodium hydride (60% in oil, 82.5 mmol) which had been washed with hexane was dispersed in 150 ml of toluene under a nitrogen atmosphere, and to this suspension was dropwise added 7.5 g of glycerol while stirring with a mechanical stirrer to precipitate sodium alcholate. After completion of the addition, the stirring was continued for 30 minutes, followed by decantation to remove toluene and an addition of 150 ml of glycerol to the residue. After stirring for 15 minutes, 15 g of 2-chloro-3,5-dinitropyridine (73.7 mmol) was added by portions under ice-cooling. The mixture was stirred for 1 hour under ice-cooling and for a further 1 hour at room temperature, followed by an addition of 35 ml of saturated aqueous solution of ammonium chloride and extraction with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was removed by evaporation and the residue was purified over silica gel column chromatography (Silica gel 60 manufactured by Merk Co.; eluent: ethyl acetate:hexane=1:1-2:1) to obtain 19 g (73.2 mmol) of the title compound in the form of a yellow solid (yield: 99%). The compound can be further purified by a mixed solvent of ethanol-ether-hexane.

Workup

  1. customto precipitate sodium alcholate
  2. additionAfter completion of the addition
  3. customto remove toluene
  4. additionan addition of 150 ml of glycerol to the residue
  5. stirringAfter stirring for 15 minutes
  6. temperaturecooling
  7. stirringThe mixture was stirred for 1 hour under ice-
  8. washThe extract was washed with saturated brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. customThe solvent was removed by evaporation
  11. customthe residue was purified over silica gel column chromatography (Silica gel 60 manufactured by Merk Co.; eluent: ethyl acetate:hexane=1:1-2:1)

Sources & evidence

ORD record
ord-3958cb6138a44d85bc1be16754e54014
Source dataset
uspto-grants-1992_01
Patent number
US05082467

Reaction notes

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