Hexaethylene Glycol → HCID 19825412, compound

HRID 2249283Notes

Reaction equation

HRID 2249283 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)=[CH:25][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][CH:25]=2)=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 17472Hexaethylene GlycolHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 685274-Bromobenzyl bromide

Product 1

HCID 19825412HCID 19825412, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 766 mg (19.2 mmol) of sodium hydride contained at 60% in mineral oil in dry dimethylformamide (40 ml) was added 1.80 g (6.38 mmol) of hexaethylene glycol in an atmosphere of argon, and the mixture was allowed to react at 40°-50° C. for 30 min. Then, 3.51 g (14.0 mmol) of 4-bromobenzyl bromide was added, and the mixture was allowed to react at room temperature for 16 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 3.64 g (5.87 mmol) of 1,21-bis(4-bromophenyl)-2,5,8,11,14,17,20-heptaoxaheneicosane.

Workup

  1. customto react at 40°-50° C. for 30 min
  2. customto react 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 dichloromethane

Sources & evidence

ORD record
ord-46f30f9317e34fb39f1989dd0402f344
Source dataset
uspto-grants-1991_08
Patent number
US05043142

Reaction notes

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