Hexaethylene Glycol → HCID 19825393, compound

HRID 2249290Notes

Reaction equation

HRID 2249290 reaction equation
[H-].[Na+].[CH2:3]([OH:21])[CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][OH:20].[Br:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27]Br)=[C:25]([CH3:31])[CH:24]=1.[Cl-].[NH4+]>CN(C)C=O>[Br:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27][O:20][CH2:19][CH2:18][O:17][CH2:16][CH2:15][O:14][CH2:13][CH2:12][O:11][CH2:10][CH2:9][O:8][CH2:7][CH2:6][O:5][CH2:4][CH2:3][O:21][CH2:27][C:26]2[CH:29]=[CH:30][C:23]([Br:22])=[CH:24][C:25]=2[CH3:31])=[C:25]([CH3:31])[CH:24]=1

Participants

6

Reactant 4

HCID 17472Hexaethylene GlycolHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 225690184-Bromo-1-(bromomethyl)-2-methylbenzene

Product 1

HCID 19825393HCID 19825393, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 354 mg (3.85 mmol) of sodium hydride contained at 60% in mineral oil in dry dimethylformamide (20 ml) was added 1.00 g (3.54 mmol) of hexaethylene glycol, and the mixture was reacted at 40°-50° C. for 30 min. Then, 2.06 g (7.79 mmol) of 4-bromo-2-methylbenzyl bromide was added, and the mixture was allowed to react at room temperature for 17 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 concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography for separation and purification. Elution with ethyl acetate-hexane (1:4) yielded 2.02 g (3.12 mmol) of 1,21-bis(4-bromo-2-methylphenyl)-2,5,8,11,14,17,20-heptaoxaheneicosane.

Workup

  1. customthe mixture was reacted at 40°-50° C. for 30 min
  2. customto react at room temperature for 17 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 acetate-hexane (1:4)

Sources & evidence

ORD record
ord-73d384f14aad415d84d7f00f4413d906
Source dataset
uspto-grants-1991_08
Patent number
US05043142

Reaction notes

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