Ethylene Glycol → HCID 18920673, compound

HRID 2249287Notes

Reaction equation

HRID 2249287 reaction equation
[H-].[Na+].[CH2:3]([OH:6])[CH2:4][OH:5].[Br:7][C:8]1[CH:15]=[CH:14][C:11]([CH2:12]Br)=[CH:10][CH:9]=1.[Cl-].[NH4+]>CN(C)C=O>[Br:7][C:8]1[CH:15]=[CH:14][C:11]([CH2:12][O:5][CH2:4][CH2:3][O:6][CH2:12][C:11]2[CH:14]=[CH:15][C:8]([Br:7])=[CH:9][CH:10]=2)=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 685274-Bromobenzyl bromide

Product 1

HCID 18920673HCID 18920673, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 603 mg (15.1 mmol) of sodium hydride contained at 60% in mineral oil in dry dimethylformamide (50 ml) was added 259 mg (4.17 mmol) of ethylene glycol in an atmosphere of argon, and the mixture was allowed to react at 40°-50° C. for 30 min. Then, 2.69 g (10.8 mmol) of 4-bromobenzyl bromide was added, and the mixture was reacted at room temperature for 20 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 1.57 g (3.93 mmol) of 1,6-bis(4-bromophenyl)-2,5-dioxahexane.

Workup

  1. customto react at 40°-50° C. for 30 min
  2. customthe mixture was reacted at room temperature for 20 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-6e8d4749139a487e9e35909ed5e405b1
Source dataset
uspto-grants-1991_08
Patent number
US05043142

Reaction notes

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