Ethylene Glycol → 2-(4-Nitrophenyl)-1,3-dioxolane

HRID 2366332Notes

Reaction equation

HRID 2366332 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:12](O)[CH2:13][OH:14].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH:8]2[O:14][CH2:13][CH2:12][O:9]2)=[CH:10][CH:11]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 5414-NitrobenzaldehydeHCID 6101p-Toluenesulfonic acid

Product 1

HCID 2667962-(4-Nitrophenyl)-1,3-dioxolaneYield 92%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred solution of p-nitrobenzaldehyde (101.5 g, 672 mmol), ethylene glycol (112 mL) and p-toluenesulfonic acid (12.8 g, 67.2 mmol) in toluene (800 mL) was heated in flask equipped with a Dean-Stark trap at 120° C. for 4 h. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. To the residue was added saturated aqueous sodium bicarbonate (800 mL) and this mixture was stirred at room temperature for 15 min. The resulting solid was isolated by filtration and dried under vacuum to give the title compound (121.8 g, 92% yield) as a yellow solid.

Workup

  1. customequipped with a Dean-Stark trap at 120° C. for 4 h
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. additionTo the residue was added saturated aqueous sodium bicarbonate (800 mL)
  4. customThe resulting solid was isolated by filtration
  5. customdried under vacuum

Sources & evidence

ORD record
ord-5096a58e47164701adc0a35f216aead4
Source dataset
uspto-grants-2014_04
Patent number
US08697724B2

Reaction notes

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