Tetraethylene Glycol → HCID 86743025, compound

HRID 1761978Notes

Reaction equation

HRID 1761978 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:13]([OH:25])[CH2:14][O:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][OH:24]>O1CCCC1>[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([C:23]([OH:24])([C:8](=[O:9])[C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=2)[CH2:22][O:21][CH2:20][CH2:19][O:18][CH2:17][CH2:16][O:15][CH2:14][CH2:13][OH:25])=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 8200Tetraethylene GlycolHCID 85024-Nitrobenzoyl chloride

Product 1

HCID 86743025HCID 86743025, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

p-Nitrobenzoyl chloride (390 g. 2.1 mole) and tetraethylene glycol (194 g, 1.0 mole) were dissolved in dry tetrahydrofuran (1 l) and the mixture evaporated under reduced pressure. The resulting thick oil was stirred under high vacuum (0.5 mm) overnight, during which time the mixture solidified. The mixture was slowly heated to 60° C. and maintained at this temperature for 5 hours. On cooling, the product was dissovled in ethyl acetate (2 l), saturated aqueous sodium bicarbonate (2 l) added and the mixture stirred at room temperature for 24 hours. The phases were separated, the organic phase washed with saturated sodium bicarbonate (3×), dried (MgSO4), filtered and the filtrate evaporated to dryness under reduced pressure. The residue was crystallized from ethyl acetate/hexanes to give bis-(4-nitrobenzoyl)-tetraethylene glycol (406 g), m.p. 57.5°-58.5° C., which was homogeneous by TLC.

Workup

  1. customthe mixture evaporated under reduced pressure
  2. temperaturemaintained at this temperature for 5 hours
  3. temperatureOn cooling
  4. additionsaturated aqueous sodium bicarbonate (2 l) added
  5. stirringthe mixture stirred at room temperature for 24 hours
  6. customThe phases were separated
  7. washthe organic phase washed with saturated sodium bicarbonate (3×)
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customthe filtrate evaporated to dryness under reduced pressure
  11. customThe residue was crystallized from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-01b43f98cd7946efbbc6acdfe1c7c087
Source dataset
uspto-grants-1989_05
Patent number
US04829099

Reaction notes

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