Diethylene Glycol → HCID 19825392, compound

HRID 2249289Notes

Reaction equation

HRID 2249289 reaction equation
[H-].[Na+].[CH2:3]([OH:9])[CH2:4][O:5][CH2:6][CH2:7][OH:8].[Br:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15]Br)=[C:13]([Cl:19])[CH:12]=1.[Cl-:20].[NH4+]>CN(C)C=O>[Br:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][O:9][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:15][C:14]2[CH:17]=[CH:18][C:11]([Br:10])=[CH:12][C:13]=2[Cl:20])=[C:13]([Cl:19])[CH:12]=1

Participants

6

Reactant 4

HCID 8117Diethylene GlycolHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 219144864-Bromo-1-(bromomethyl)-2-chlorobenzene

Product 1

HCID 19825392HCID 19825392, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 472 mg (11.8 mmol) of sodium hydride contained at 60% in mineral oil in dry dimethylformamide (50 ml) was added 500 mg (4.71 mmol) of diethylene glycol in an atmosphere of argon, and the mixture was allowed to react at 40°-50° C. for 30 min. Then, 2.96 g (10.4 mmol) of 4-bromo-2-chlorobenzyl bromide was added, and the mixture was reacted at room temperature for 16 hours. To the reaction solution at 0° C. was added a saturated aqueous solution of ammonium chloride followed by extraction with ethyl acetate. The organic layer was washed with water and then concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography for separation and purification. Elution with ethyl acetatehexane (1:3) yielded 2.10 g (4.09 mmol) of 1,9-bis(4-bromo-2-chlorophenyl)-2,5,8-trioxanonane.

Workup

  1. customto react at 40°-50° C. for 30 min
  2. customthe mixture was reacted at room temperature for 16 hours
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with water
  5. concentrationconcentrated under reduced pressure
  6. customThe residue thus obtained
  7. customwas subjected to silica gel column chromatography for separation and purification
  8. washElution with ethyl acetatehexane (1:3)

Sources & evidence

ORD record
ord-72b1fce3b98f45a1a7edabb54c8c6fce
Source dataset
uspto-grants-1991_08
Patent number
US05043142

Reaction notes

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