Triethylene Glycol → HCID 19825347, compound

HRID 2249282Notes

Reaction equation

HRID 2249282 reaction equation
[H-].[Na+].[CH2:3]([OH:12])[CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][OH:11].[Br:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Br)=[CH:16][CH:15]=1.[Cl-].[NH4+]>CN(C)C=O>[Br:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][O:12][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:18][C:17]2[CH:20]=[CH:21][C:14]([Br:13])=[CH:15][CH:16]=2)=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 8172Triethylene GlycolHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 685274-Bromobenzyl bromide

Product 1

HCID 19825347HCID 19825347, compoundYield 90.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 355 mg (8.88 mmol) of sodium hydride contained at 60% in mineral oil in dry dimethylformamide (60 ml) was added 851 mg (5.67 mmol) of triethylene glycol in an atmosphere of argon, and the mixture was reacted at 40°-50° C. for 30 min. followed by addition of 3.37 g (13.5 mmol) of 4-bromobenzyl bromide. The mixture was allowed to react at room temperature for 18 hours. To the reaction mixture 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 dichloromethane yielded 2.51 g (5.14 mmol) of 1,12-bis(4-bromophenyl)-2,5,8,11-tetraoxadodecane.

Workup

  1. customthe mixture was reacted at 40°-50° C. for 30 min.
  2. customto react at room temperature for 18 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 dichloromethane

Sources & evidence

ORD record
ord-0361b8e2fa0d4037af74549c22129c45
Source dataset
uspto-grants-1991_08
Patent number
US05043142

Reaction notes

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