Ethylene Glycol → HCID 68522210, compound

HRID 884090Notes

Reaction equation

HRID 884090 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:10][C:11]2[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][CH:12]=2)=[N:8][CH:9]=1)([O-:3])=[O:2].[CH2:19](O)[CH2:20][OH:21].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH2:20]1[O:21][CH:15]([C:14]2[CH:17]=[CH:18][C:11]([O:10][C:7]3[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][N:8]=3)=[CH:12][CH:13]=2)[O:16][CH2:19]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 797796HCID 797796, compound

Product 1

HCID 68522210HCID 68522210, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 4-[(5-nitro-2-pyridyl)oxy]benzaldehyde (5.00 g, 20.5 mmol) in benzene (100 mL) were added ethylene glycol (2.28 mL, 41.0 mmol) and p-toluenesulfonic acid (0.50 g), and the resulting solution was heated to reflux for 3 hours while removing water with a Dean-Stark. The reaction solution was washed with a saturated sodium bicarbonate solution, and subsequently washed with brine. The benzene layer was dried over anhydrous magnesium sulfate, and evaporated, to thereby yield 5.88 g of the title compound.

Workup

  1. temperaturethe resulting solution was heated
  2. temperatureto reflux for 3 hours
  3. customwhile removing water with a Dean-Stark
  4. washThe reaction solution was washed with a saturated sodium bicarbonate solution
  5. washsubsequently washed with brine
  6. dry with materialThe benzene layer was dried over anhydrous magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-13d6fbe68c844198bce8fcd356410f88
Source dataset
uspto-grants-2012_08
Patent number
US08236826B2

Reaction notes

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